- N-acylcarbazole as a selective transamidation reagent
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N-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that N-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with N-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an N-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with N-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.
- Kang, Bubwoong,Kuse, Masaki,Okamura, Hironori,Sakai, Asumi,Satoh, Tetsuya,Shinada, Tetsuro,Yasuno, Yoko
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p. 993 - 999
(2020/09/22)
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- Characterization of arylalkylamine n-acyltransferase from tribolium castaneum: an investigation into a potential next-generation insecticide target
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The growing issue of insecticide resistance has meant the identification of novel insecticide targets has never been more important. Arylalkylamine N-acyltransferases (AANATs) have been suggested as a potential new target. These promiscuous enzymes are involved in the N-acylation of biogenic amines to form N-acylamides. In insects, this process is a key step in melanism, hardening of the cuticle, removal of biogenic amines, and in the biosynthesis of fatty acid amides. The unique nature of each AANAT isoform characterized indicates each organism accommodates an assembly of discrete AANATs relatively exclusive to that organism. This implies a high potential for selectivity in insecticide design, while also maintaining polypharmacology. Presented here is a thorough kinetic and structural analysis of AANAT found in one of the most common secondary pests of all plant commodities in the world, Tribolium castaneum. The enzyme, named TcAANAT0, catalyzes the formation of short-chain N-acylarylalkylamines, with short-chain acyl-CoAs (C2-C10), benzoyl-CoA, and succinyl-CoA functioning in the role of acyl donor. Recombinant TcAANAT0 was expressed and purified from E. coli and was used to investigate the kinetic and chemical mechanism of catalysis. The kinetic mechanism is an ordered sequential mechanism with the acyl-CoA binding first. pH-rate profiles and site-directed mutagenesis studies identified amino acids critical to catalysis, providing insights about the chemical mechanism of TcAANAT0. A crystal structure was obtained for TcAANAT0 bound to acetyl-CoA, revealing valuable information about its active site. This combination of kinetic analysis and crystallography alongside mutagenesis and sequence analysis shines light on some approaches possible for targeting TcAANAT0 and other AANATs for novel insecticide design.
- Anderson, Ryan L.,Chen, Yu,Gelis, Ioannis,Leahy, James W.,Lewandowski, Eric M.,Mccaskey, Angelica N.,Merkler, David J.,O'flynn, Brian G.,Prins, Karin Claire,Rios-Guzman, Nasha M.,Shepherd, Britney A.,Suarez, Gabriela
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p. 513 - 523
(2020/03/11)
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- Bifunctional thiosquaramide catalyzed asymmetric reduction of dihydro-β-carbolines and enantioselective synthesis of (-)-coerulescine and (-)-horsfiline by oxidative rearrangement
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Tetrahydro-β-carboline (THBC) is a tricyclic ring system that can be found in a large number of bioactive alkaloids. Herein, we report a simple and efficient method for the synthesis of enantiopure THBCs through a chiral thiosquaramide (11b) catalyzed imine reduction of dihydro-β-carbolines (17a-f). The in situ generated Pd-H employed as hydride source in the reaction of differently substituted chiral THBCs (18a-f) afforded high selectivities (R isomers, up to 96% ee) and good isolated yields (up to 88%). Moreover, the chiral thiosquaramide used also afforded exceptional catalyst activity in the syntheses of (-)-coerulescine (5) and (-)-horsfiline (6) with excellent enantioselectivities up to 98% and 93% ee, respectively, via an enantioselective oxidative rearrangement approach.
- Nachtigall, Fabiane M.,Santos, Leonardo S.,Sathish, Manda
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p. 38672 - 38677
(2020/11/05)
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- A metal-free approach for the synthesis of amides/esters with pyridinium salts of phenacyl bromides via oxidative C–C bond cleavage
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An efficient, simple, and metal-free synthetic approach for the N- and O-benzoylation of various amines/benzyl alcohols with pyridinium salts of phenacyl bromides is demonstrated to generate the corresponding amides and esters. This protocol facilitates the oxidative cleavage of a C–C bond followed by formation of a new C–N/C–O bond in the presence of K2CO3. Various pyridinium salts of phenacyl bromides can be readily transformed into a variety of amides and esters which is an alternative method for the conventional amidation and esterification in organic synthesis. High functional group tolerance, broad substrate scope and operational simplicity are the prominent advantages of the current protocol.
- Manasa, Kesari Lakshmi,Tangella, Yellaiah,Krishna, Namballa Hari,Alvala, Mallika
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p. 1864 - 1871
(2019/08/12)
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- Base-Promoted Amidation and Esterification of Imidazolium Salts via Acyl C-C bond Cleavage: Access to Aromatic Amides and Esters
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Imidazolium salts have been effectively employed as suitable acyl transfer agents in amidation and esterification in organic synthesis. The weak acyl C(O)-C imidazolium bond was exploited to generate acyl electrophiles, which further react with amines and alcohols to afford amides and esters. The broad substrate scope of anilines and benzylic amines and base-promoted conditions are the benefits of this route. Interestingly, phenol, benzylic alcohols, and a biologically active alcohol can also be subjected to esterification under the optimized conditions.
- Karthik, Shanmugam,Muthuvel, Karthick,Gandhi, Thirumanavelan
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p. 738 - 751
(2019/01/24)
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- The magnetic graphene oxide/NHC catalyzed aerobic direct amidation and cross-dehydrogenative coupling of aldehydes
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In this paper, the synthesis of a novel imidazolium based N-heterocyclic carbene (NHC) containing imidazopyridine substitutes using a three-component reaction is described. This compound was immobilized on magnetic graphene oxide (GO) to make a heterogeneous catalyst for the direct aerobic amidation of benzaldehyde derivatives under solvent-free conditions, as well as the intra-and intermolecular cross dehydrogenative coupling of aldehydes. In addition, the catalytic activity of the NHC catalyst was homogeneously studied in the presence of Fe3O4 nanoparticles under the same conditions, and showed good activity with lower yields than the heterogeneous catalyst.
- Sepahvand, Heshmatollah,Ghasemi, Elnaz,Sharbati, Mohammad,Mohammadi, Melika Sadat,Arshadi Pirlar, Maghsoud,Shahverdizadeh, Gholam Hossein
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p. 16555 - 16565
(2019/11/11)
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- Aryl substituted amide compounds and its preparation method, pharmaceutical composition containing the same and application thereof (by machine translation)
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The invention relates to an aryl-substituted amide compound in the formula (I), a preparing method thereof, a medicine composition comprising the same, and application of the amide compound and the medicine composition to pharmacy, wherein Arl, L1, M1, M2, L2 and Ar2 are defined as in the text. The aryl-substituted amide compound can excite TRPV1 and nuclear receptors (LXRs, PPARs and RXR), adjust expression of cholesterol excretion gap-associated protein ABCA1/G1, SR-BI, adjust expression of inflammation gap-associated protein TNF-alpha and the like, and play roles in promoting excretion of cholesterol and lipid, reducing sugar, adjusting blood lipid, resisting inflammation and reducing blood pressure, and can be used for treating and/or preventing and/or relieving cardiovascular and cerebrovascular diseases, adjusting blood lipid, and resisting atherosclerosis, diabetes mellitus, inflammation, pain and hypertension.
- -
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Paragraph 0111; 0126; 0127
(2018/07/30)
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- Rational design of a new class of toll-like receptor 4 (tlr4) tryptamine related agonists by means of the structure- and ligand-based virtual screening for vaccine adjuvant discovery
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In order to identify novel lead structures for human toll-like receptor 4 (hTLR4) modulation virtual high throughput screening by a peta-flops-scale supercomputer has been performed. Based on the in silico studies, a series of 12 compounds related to tryptamine was rationally designed to retain suitable molecular geometry for interaction with the hTLR4 binding site as well as to satisfy general principles of drug-likeness. The proposed compounds were synthesized, and tested by in vitro and ex vivo experiments, which revealed that several of them are capable to stimulate hTLR4 in vitro up to 25% activity of Monophosphoryl lipid A. The specific affinity of the in vitro most potent substance was confirmed by surface plasmon resonance direct-binding experiments. Moreover, two compounds from the series show also significant ability to elicit production of interleukin 6.
- Honegr, Jan,Dolezal, Rafael,Malinak, David,Benkova, Marketa,Soukup, Ondrej,De Almeida, Joyce S. F. D.,Franca, Tanos C. C.,Kuca, Kamil,Prymula, Roman
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- An Unconventional Reaction of 2,2-Diazido Acylacetates with Amines
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We have discovered that 2,2-diazido acylacetates, a class of compounds with essentially unknown reactivity, can be coupled to amines through a new strategy that does not involve any reagents. 2,2-Diazido acetate is the unconventional leaving group under carbon–carbon bond cleavage. This reaction leads to the construction of amide bonds, tolerates various functionalities and is performed equally well in numerous solvents under experimentally simple conditions. We also demonstrate that the isolation of the 2,2-diazido acylacetate compounds can be circumvented: Acylacetates were easily fragmented when treated with (Bu4N)N3 and iodine in the presence of an amine at room temperature. By using this method, a broad range of acylacetates with various structural motifs were directly transformed into amides.
- H?ring, Andreas P.,Biallas, Phillip,Kirsch, Stefan F.
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supporting information
p. 1526 - 1539
(2017/04/01)
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- One-pot synthesis of tricyclo-1,4-benzoxazines via visible-light photoredox catalysis in continuous flow
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A facile one-pot synthesis of tricyclo-1,4-benzoxazines has been developed via metal-free intramolecular cyclization of indole derivates. These reactions were efficiently achieved at ambient temperature by using visible-light photoredox catalysis in conti
- Wu, Guolin,Lv, Tingting,Mo, Wenhui,Yang, Xiping,Gao, Yu,Chen, Haijun
-
supporting information
p. 1395 - 1398
(2017/03/16)
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- Synthetic study on the T3P-promoted one-pot preparation of 1-substituted-3,4-dihydro-β-carbolines by the reaction of tryptamine with carboxylic acids
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A novel and efficient one-pot method has been developed for the synthesis of 1-substituted-3,4-dihydro-β-carbolines from tryptamine and a wide variety of carboxylic acids. The reaction was successfully applied to the synthesis of an important alkaloid har
- ábrányi-Balogh, Péter,F?ldesi, Tamás,Grün, Alajos,Volk, Balázs,Keglevich, Gy?rgy,Milen, Mátyás
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supporting information
p. 1953 - 1957
(2016/04/20)
-
- A Robust, Recyclable Resin for Decagram Scale Resolution of (±)-Mefloquine and Other Chiral N-Heterocycles
-
Decagram quantities of enantiopure (+)-mefloquine have been produced via kinetic resolution of racemic mefloquine using a ROMP-gel supported chiral acyl hydroxamic acid resolving agent. The requisite monomer was prepared in a few synthetic steps without chromatography and polymerization was safely performed on a >30 gram scale under ambient conditions. The reagent was readily regenerated and reused multiple times for the resolution of 150 grams of (±)-mefloquine and other chiral N-heterocylces.
- Kreituss, Imants,Chen, Kuang-Yen,Eitel, Simon H.,Adam, Jean-Michel,Wuitschik, Georg,Fettes, Alec,Bode, Jeffrey W.
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supporting information
p. 1553 - 1556
(2016/02/12)
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- Synthesis of naked amino-pyrroloindoline via direct aminocyclization of tryptamine
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The first direct access to unprotected amino-pyrroloindoline via aminocyclization of tryptamine and tryptophan has been described. A variety of structurally diverse amino-pyrroloindolines are furnished by the use of O-(2,4-dinitrophenyl)hydroxylamine (DPH
- Shen, Zhigao,Xia, Zilei,Zhao, Huijun,Hu, Jiadong,Wan, Xiaolong,Lai, Yisheng,Zhu, Chen,Xie, Weiqing
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supporting information
p. 5381 - 5384
(2015/05/20)
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- Benzoic acid-catalyzed transamidation reactions of carboxamides, phthalimide, ureas and thioamide with amines
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An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal-free conditions is described. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines.
- Wu, Ji-Wei,Wu, Ya-Dong,Dai, Jian-Jun,Xu, Hua-Jian
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supporting information
p. 2429 - 2436
(2014/09/30)
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- An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin y
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A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation-Bischler- Napieralski reaction conditions using tryptamine and 2,2-dibromo-1- phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.
- Meruva, Suresh Babu,Raghunadh, Akula,Kamaraju, Raghavendra Rao,Kumar, U.K. Syam,Dubey
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p. 471 - 480
(2014/03/21)
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- Optimization of rutaecarpine as ABCA1 up-regulator for treating atherosclerosis
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ATP-binding cassette transporter A1 (ABCA1) is a key transporter and receptor in promoting cholesterol efflux, and increasing the expression level of ABCA1 is antiatherogenic. In our previous study, rutaecarpine (RUT) was found to protect ApoE-/- mice from developing atherosclerosis through preferentially up-regulating ABCA1 expression. In the present work, a series of RUT derivatives were synthesized and examined as ABCA1 expression up-regulators. Compounds CD1, CD6, and BCD1-2 were found to possess the most potential activity as antiatherosclerotic agents among all compounds tested.
- Li, Yongzhen,Feng, Tingting,Liu, Peng,Liu, Chang,Wang, Xiao,Li, Dongsheng,Li, Ni,Chen, Minghua,Xu, Yanni,Si, Shuyi
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supporting information
p. 884 - 888
(2014/09/17)
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- Chiral anion phase transfer of aryldiazonium cations: An enantioselective synthesis of C3-diazenated pyrroloindolines
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Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air- and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core. Live and let diazene: Chiral anion phase transfer of aryldiazonium cations has been utilized to prepare C3-diazenated pyrroloindolines. The air- and water-tolerant reaction allows electronic and steric diversity in the aryldiazonium electrophile and the tryptamine core, with the products being obtained in up to 99% yield and 96% ee (MTBE=methyl tert-butyl ether).
- Nelson, Hosea M.,Reisberg, Solomon H.,Shunatona, Hunter P.,Patel, Jigar S.,Toste, F. Dean
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supporting information
p. 5600 - 5603
(2014/06/10)
-
- Stereoselective bioreduction of β-carboline imines through cell-free extracts from earthworms (Eisenia foetida)
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Although remarkable advances have been made over the last decade in organic synthesis, catalysis, and biotechnology, there is still a need to introduce and develop new processes for chemical production to achieve sustainable and cleaner approaches to support the increasing global pharmaceutical/chemical industry. There is a growing need to produce optically active compounds in high yields to maintain and support areas such as pharmaceutical and natural product synthesis. Thus, chemists today are looking for alternative reactions carried out under green conditions. In this context, we describe β-carboline imine reductions employing cell-free extracts from red Californian earthworms (Eisenia foetida) in high yields and enantiomeric excesses. The enantiomeric excess values of the bioreduction showed no dependence on the imine 1a-g substituents to afford amines with an (R)-configuration. Based on these data, a model for the cell-free extract from the earthworm is proposed.
- Mirabal-Gallardo, Yaneris,Soriano, Maria Del Pilar C.,Santos, Leonardo S.
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p. 440 - 443
(2013/06/27)
-
- 1-Benzyl-1,2,3,4-Tetrahydro-β-Carboline as Channel Blocker of N-Methyl-d-Aspartate Receptors
-
N-methyl-d-aspartate (NMDA) receptors belong to the family of ligand-gated ion channels and are important for synaptic plasticity and memory function. The NMDA receptor consists of a voltage-dependent channel permeable to Ca2+ and Na+/sup
- Espinoza-Moraga, Marlene,Caballero, Julio,Gaube, Friedemann,Winckler, Thomas,Santos, Leonardo S.
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experimental part
p. 594 - 599
(2012/06/29)
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- Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus
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β-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compoun
- Espinoza-Moraga, Marlene,Petta, Tania,Vasquez-Vasquez, Marco,Laurie, V. Felipe,Moraes, Luis A.B.,Santos, Leonardo Silva
-
body text
p. 1988 - 1992
(2010/11/05)
-
- Palladium asymmetric reduction of β-carboline imines mediated by chiral auxiliaries assisted by microwave irradiation
-
An alternative synthetic approach for the introduction of chirality in β-carboline moiety through in situ reduction of N-acyliminium ion intermediates generated from imine 2 and chloroformate of 8-phenylmenthyl as chiral auxiliary was achieved. The method applied microwave-assisted irradiation and used PdCl2/Et3SiH protocol as a mild reducing agent, which decreased reaction times to minutes when compared to the conventional thermal reactions. The diastereoselectivity (4-12:1) of the reduction produced R-amines, which were assigned after chiral auxiliary removal and spectroscopic data compared to products obtained from Noyori asymmetric hydrogenation catalyst.
- Espinoza-Moraga, Marlene,Caceres, Ana Gloria,Santos, Leonardo Silva
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scheme or table
p. 7059 - 7061
(2010/02/28)
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- N-[(Dihydroxyphenyl)acyl]serotonins as potent inhibitors of tyrosinase from mouse and human melanoma cells
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A series of N-acyl derivatives of tyramine, tryptamine, and serotonin were synthesized and tested on anti-melanogenic activity. The serotonin derivatives such as N-caffeoylserotonin (3) and N-protocatechuoylserotonin (9) were inhibitory to tyrosinase from
- Yamazaki, Yoshimitsu,Kawano, Yasuhiro,Yamanaka, Akiko,Maruyama, Susumu
-
body text
p. 4178 - 4182
(2010/04/26)
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- A highly enantioselective access to tetrahydroisoquinoline and β-carboline alkaloids with simple noyori-type catalysts in aqueous media
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Silver enhancement: A very convenient modified protocol for the enantioselective transfer hydrogenation of dihydroisoquinoline skeletons under aqueous conditions is reported. Unmodified Noyori ligands can be used and the activity of the catalyst is greatly enhanced with silver additives (see scheme). The protocol was used in a very short synthesis of the alkaloids (S)-harmicine and (S)-crispine.
- Evanno, Laurent,Ormala, Joel,Pihko, Petri M.
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supporting information; experimental part
p. 12963 - 12967
(2010/06/16)
-
- M4 agonists/5HT7 antagonists with potential as antischizophrenic drugs: Serominic compounds
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Chronic low-dose treatment of rats with the psychomimetic drug, phencyclidine, induces regionally specific metabolic and neurochemical changes in the CNS that mirror those observed in the brains of schizophrenic patients. Recent evidence suggests that drugs targeting serotoninergic and muscarinic receptors, and in particular 5-HT7 antagonists and M4 agonists, exert beneficial effects in this model of schizophrenia. Compounds that display this combined pattern of activity we refer to as serominic compounds. Based upon leads from natural product screening, we have designed and synthesised such serominic compounds, which are principally arylamidine derivatives of tetrahydroisoquinolines, and shown that they have the required serominic profile in ligand binding assays and show potential antipsychotic activity in functional assays.
- Suckling, Colin J.,Murphy, John A.,Khalaf, Abedawn I.,Zhou, Sheng-ze,Lizos, Dimitris E.,van Nhien, Albert Nguyen,Yasumatsu, Hiroshi,McVie, Allan,Young, Louise C.,McCraw, Corinna,Waterman, Peter G.,Morris, Brian J.,Pratt, Judith A.,Harvey, Alan L.
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p. 2649 - 2655
(2008/02/02)
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- Asymmetric transfer hydrogenation of imines and iminiums catalyzed by a water-soluble catalyst in water
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The first asymmetric transfer hydrogenation of cyclic imines and iminiums in water was successfully performed in high yields and enantioselectivities with sodium formate as the hydrogen source and CTAB as an additive catalyzed by a water-soluble and recyc
- Wu, Jiashou,Wang, Fei,Ma, Yaping,Cui, Xin,Cun, Linfeng,Zhu, Jin,Deng, Jingen,Yu, Bangliang
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p. 1766 - 1768
(2008/03/27)
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- Reactions of indoles with nitrogen dioxide and nitrous acid in an aprotic solvent
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The reaction of 2-phenyl- and 1-methyl-2-phenylindole with nitrogen dioxide or with nitrous acid (NaNO2-CH3COOH) in benzene leads mainly to the formation of the isonitroso and 3-nitroso indole derivatives, respectively. When reacted
- Astolfi, Paola,Panagiotaki, Maria,Rizzoli, Corrado,Greci, Lucedio
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p. 3282 - 3290
(2008/09/17)
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- (PhO)3P·Cl2-promoted bischler-napieralski-type cyclization: A mild access to β-carbolines
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A novel mild access to the β-carboline skeleton is described. The reaction is a Bischler-Napieralski-type cyclocondensation, promoted by (PhO)3P·Cl2, which is performed in dichloromethane at -30 °C. The products are easily obtained i
- Spaggiari, Alberto,Davoli, Paolo,Blaszczak, Larry C.,Prati, Fabio
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p. 661 - 663
(2007/10/03)
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- Chemistry and biology of diazonamide A: Second total synthesis and biological investigations
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As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development of several special strategies and tactics. We also disclose our complete studies regarding the chemical biology of diazonamide A and its structural congeners, and more fully delineate the scope of our protocol for Robinson-Gabriel cyclodehydration using pyridine-buffered POCl 3.
- Nicolaou,Hao, Junliang,Reddy, Mali V.,Rao, Paraselli Bheema,Rassias, Gerasimos,Snyder, Scott A.,Huang, Xianhai,Chen, David Y.-K.,Brenzovich, William E.,Giuseppone, Nicolas,Giannakakou, Paraskevi,O'Brate, Aurora
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p. 12897 - 12906
(2007/10/03)
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- An improved synthesis of canthin-6-one
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An improved route has been devised which provides canthin-6-one in the highest yield from tryptamine to date. Tryptamine is converted to Nb-benzyltryptamine via reaction with benzoylchloride and reduction using LAH. Pictet-Spengler condensation with 2-ketoglutaric acid, removal of the protecting group by CTH, and aromatization with MnO2 affords canthin-6-one in 48% overall yield.
- Czerwinski, Kevin M.,Zificsak, Craig A.,Stevens, John,Oberbeck, Melissa,Randlett, Christopher,King, Melissa,Mennen, Steve
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p. 1225 - 1231
(2007/10/03)
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- Synthesis of a novel, recyclable, solid-phase acylating reagent.
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In this paper, we describe the synthesis of N-(6-cyano-1,3-dimethyl-2,4-dioxo-5-substituted-1,3-dihydropyridino[2,3-d] pyrimidin-7-yl)imides 1. We will show the synthesis of 1 using both conventional heating and microwave techniques. In addition, the imide was attached to polystyrene and this immobilized imide was equally as effective at acylating various primary and secondary amines as its solution-phase counterpart.
- Nicewonger, Robert B,Ditto, Lori,Kerr, Doug,Varady, Laszlo
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p. 1799 - 1802
(2007/10/03)
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- Solid-supported chloro[1,3,5]triazine. A versatile new synthetic auxiliary for the synthesis of amide libraries
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(equation presented) 2,4,6-Trichloro[1,3,5]triazine was loaded on different types of NH2-functionalized resins to give a new supported reagent. The best results, in term of yields products, were obtained using the chlorotriazine linked to a polystyrene-poly(ethylene glycol) resin. This reagent was employed for the solution-phase synthesis of different amides and dipeptides.
- Masala, Simonetta,Taddei, Maurizio
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p. 1355 - 1357
(2008/02/09)
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- On a facile synthesis of melatonin and other related indoles
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An efficient laboratory synthesis for melatonin and other related indoles utilising enamides and enecarbamates is described.
- Marais, Wilhelmina,Holzapfel, Cedric W.
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p. 3681 - 3691
(2007/10/03)
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- One-Pot Synthesis of Indoles from 1-Benzyl-2,3-dihydroindoles
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A facile one-pot dehydrodebenzylation of 1-benzyl-2,3-dihydroindoles to indoles uses 10percent palladium on carbon as catalyst and ammonium formate as hydrogen donor in methanol.
- Kiguchi, Toshiko,Kuninobu, Naoko,Takahashi, Yoshiko,Yoshida, Yukiyo,Naito, Takeaki,Ninomiya, Ichiya
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p. 778 - 781
(2007/10/02)
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- Dehydrogenation of Indolines to Indoles via Azasulphonium Salts or N-Chloramines
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The dehydrogenation of indolines to indoles without using mineral oxidising reagents is described.The conversion was achieved via either azasulphonium salts or N-chloramines, the former route involving milder conditions but a more complex procedure.
- Kawase, Masami,Miyake, Yuko,Kikugawa, Yasuo
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p. 1401 - 1404
(2007/10/02)
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- A GENERAL METHOD FOR THE SYNTHESIS OF INDOLES BEARING A VARIETY OF SUBSTITUENTS AT THE β-POSITION, AND ITS APPLICATION TO THE SYNTHESIS OF L-TRYPTOPHAN
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A general synthetic method of β-substituted indoles such as indolacetic acid, tryptamine and L-tryptophan has been exploited utilizing α-methoxylated amides, lactams, a carbamate, and sulfonamides, easily obtainable by an electrochemical method, as key intemediates.
- Shono, Tatsuya,Matsumura, Yoshihiro,Kanazawa, Takenobu
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p. 1259 - 1262
(2007/10/02)
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- A NEW DEHYDROGENATION REACTION OF INDOLINES TO INDOLES VIA AZASULFONIUM SALTS
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Indolines (1) have been converted to the corresponding azasulfonium salts (2) and the subsequent intramolecular base catalyzed abstraction of the hydrogen at C-2 gave indoles (4) in good yields.
- Kikugawa, Yasuo,Kawase, Masami
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p. 445 - 446
(2007/10/02)
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- Synthesis of Oxazolylindole Alkaloids from Tryptamine and Tryptophan by Oxidation with 2,3-Dichloro-5,6-dicyanobenzoquinone
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When N-acyl derivatives of tryptamine and L-tryptophan methyl ester were treated with DDQ (2 equiv) in tetrahydrofuran or other anhydrous solvents, four consecutive reactions, dehydrogenation, nucleophilic cyclization, another dehydrogenation, and isomeri
- Yoshioka, Tadao,Mohri, Kunihiko,Oikawa, Yuji,Yonemitsu, Osamu
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p. 2252 - 2281
(2007/10/02)
-