- Photoredox-Mediated Reaction of gem-Diborylalkenes: Reactivity Toward Diverse 1,1-Bisborylalkanes
-
The use of gem-diborylalkenes as radical-reactive groups is explored for the first time. These reactions provide an efficient and general method for the photochemical conversion of gem-diborylalkenes to rapidly access 1,1-bisborylalkanes. This method expl
- Eghbarieh, Nadim,Kumar, Nivesh,Masarwa, Ahmad,Shames, Alexander I.,Stein, Tamar
-
supporting information
p. 5360 - 5364
(2020/04/23)
-
- Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis
-
Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.
- Morisset, Eléonore,Chardon, Aurélien,Rouden, Jacques,Blanchet, Jér?me
-
supporting information
p. 388 - 392
(2020/01/24)
-
- Synthesis and biological evaluation of a novel series of curcumin-peptide derivatives as PepT1-mediated transport drugs
-
Curcumin (CUR) is a natural yellow pigment from turmeric with extensive bioactivities. However its relatively poor solubility limited its absorption and bioavailability. In this study, a novel series of CUR-peptide conjugates were designed and synthesized
- Zhang, Jiyun,Wen, Hongmei,Shen, Fei,Wang, Xinzhi,Shan, Chenxiao,Chai, Chuan,Liu, Jian,Li, Wei
-
-
- TCFH-NMI: Direct Access to N-Acyl Imidazoliums for Challenging Amide Bond Formations
-
Challenging couplings of hindered carboxylic acids with non-nucleophilic amines to form amide bonds can be accomplished in high yields, and in many cases, with complete retention of the adjacent stereogenic centers using the combination of N,N,N′,N′-tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI). This method allows for in situ generation of highly reactive acyl imidazolium ions, which have been demonstrated to be intermediates in the reaction. The reagent delivers high reactivity similar to acid chlorides with the ease of use of modern uronium reagents.
- Beutner, Gregory L.,Young, Ian S.,Davies, Merrill L.,Hickey, Matthew R.,Park, Hyunsoo,Stevens, Jason M.,Ye, Qingmei
-
supporting information
p. 4218 - 4222
(2018/07/29)
-
- Sequential One-Pot Synthesis of Dipeptides through the Transient Formation of CDI-N-Protected α-Aminoesters
-
The synthesis of dipeptides through a sequential one-pot procedure from commercially available protected amino acids is described. The transformation relies on the use of in situ generated transiently CDI-protected α-amino esters (CDI, e.g. N,N′-carbonyldiimidazole). In addition of being a highly atom-economical process, the couplings take place under very mild and neutral conditions without adding a base to the reaction medium. This protocol provides a concise and less costly route to dipeptide derivatives (12 examples, up to 87% yield) and is compatible with commonly used N-urethane protecting groups. Moreover, no epimerization was detected even when sensitive Boc-Cys(Bn)?OH was used. (Figure presented.).
- de Figueiredo, Renata Marcia,Suppo, Jean-Simon,Midrier, Camille,Campagne, Jean-Marc
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supporting information
p. 1963 - 1968
(2017/06/09)
-
- Iodine-Mediated Oxidative Coupling of Hydroxamic Acids with Amines towards a New Peptide-Bond Formation
-
An efficient and straightforward approach for the coupling of Nα-protected hydroxamic acids with an amino component in the presence of iodine is delineated. The reaction is mediated by the formation of unstable but reactive acyl nitroso intermediates. The peptide hydroxamic acids were found to be useful substrates in coupling reactions.
- Krishnamurthy, Muniyappa,Vishwanatha,Panguluri, Nageswara Rao,Panduranga,Sureshbabu, Vommina V.
-
supporting information
p. 2565 - 2569
(2015/11/16)
-
- Highly stereoselective synthesis of natural-product-like hybrids by an organocatalytic/multicomponent reaction sequence
-
In an endeavor to provide an efficient route to natural product hybrids, described herein is an efficient, highly stereoselective, one-pot process comprising an organocatalytic conjugate addition of 1,3-dicarbonyls to α,β-unsaturated aldehydes followed by
- Echemendía, Radell,De La Torre, Alexander F.,Monteiro, Julia L.,Pila, Michel,Corrêa, Arlene G.,Westermann, Bernhard,Rivera, Daniel G.,Paix?o, Márcio W.
-
supporting information
p. 7621 - 7625
(2015/06/25)
-
- Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties
-
Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.
- Laville, Rmi,Nguyen, Thanh Binh,Moriou, Cline,Petek, Sylvain,Debitus, Ccile,Al-Mourabit, Ali
-
p. 1351 - 1366
(2015/03/04)
-
- Borinic acid catalysed peptide synthesis
-
The catalytic synthesis of peptides is a major challenge in the modern organic chemistry hindered by the well-established use of stoichiometric coupling reagents. Herein, we describe for the first time that borinic acid is able to catalyse this reaction under mild conditions with an improved activity compared to our recently developed thiophene-based boronic acid. This catalyst is particularly efficient for peptide bond synthesis affording dipeptides in good yields without detectable racemization.
- El Dine, Tharwat Mohy,Rouden, Jacques,Blanchet, Jér?me
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supporting information
p. 16084 - 16087
(2015/11/10)
-
- Catalytic chemical amide synthesis at room temperature: One more step toward peptide synthesis
-
An efficient method has been developed for direct amide bond synthesis between carboxylic acids and amines via (2-(thiophen-2-ylmethyl)phenyl)boronic acid as a highly active bench-stable catalyst. This catalyst was found to be very effective at room temperature for a large range of substrates with slightly higher temperatures required for challenging ones. This methodology can be applied to aliphatic, α-hydroxyl, aromatic, and heteroaromatic acids as well as primary, secondary, heterocyclic, and even functionalized amines. Notably, N-Boc-protected amino acids were successfully coupled in good yields with very little racemization. An example of catalytic dipeptide synthesis is reported.
- Mohy El Dine, Tharwat,Erb, William,Berhault, Yohann,Rouden, Jacques,Blanchet, Jér?me
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p. 4532 - 4544
(2015/05/13)
-
- Inverse peptide synthesis via activated α-aminoesters
-
A mild, practical, and simple procedure for peptide-bond formation is reported. Instead of activation of the carboxylic acid functionality, the reaction involves an unprecedented use of activated α-aminoesters. The method provides a straightforward entry to dipeptides and was effective when a sensitive cysteine residue was used, as no epimerization was detected in this case. The applicability of this method to iterative peptide synthesis was illustrated by the synthesis of a model tetrapeptide in the challenging reverse N→C direction. How to advance by going into reverse: In a mild and practical procedure for peptide-bond formation, free α-aminoesters were activated by treatment with N,N′-carbonyldiimidazole, instead of activating the carboxylic acid functionality (see scheme). The method provided a straightforward route to dipeptides, and its applicability to iterative peptide synthesis was illustrated by the synthesis of a tetrapeptide in the challenging reverse N→C direction.
- Suppo, Jean-Simon,Subra, Gilles,Berges, Matthieu,Marcia De Figueiredo, Renata,Campagne, Jean-Marc
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supporting information
p. 5389 - 5393
(2014/06/09)
-
- Thioacetic acid/NaSH-mediated synthesis of N -protected amino thioacids and their utility in peptide synthesis
-
Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.
- Mali, Sachitanand M.,Gopi, Hosahudya N.
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p. 2377 - 2383
(2014/04/17)
-
- Processes for forming amide bonds and compositions related thereto
-
The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.
- -
-
Page/Page column 23; 24
(2015/01/07)
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- Se -(9-fluorenylmethyl) selenoesters; Preparation, reactivity, and use as convenient synthons for selenoacids
-
Se-(9-Fluorenylmethyl) selenoesters are readily prepared, stable precursors to selenocarboxylates, which they liberate on treatment with DBU. Fm selenoesters are compatible with the use of TFA for the removal of Boc groups and with simple peptide bond for
- Fecourt, Fabien,Delpech, Bernard,Melnyk, Oleg,Crich, David
-
supporting information
p. 3758 - 3761
(2013/08/23)
-
- Design, synthesis and biological evaluation of novel L-isoserine tripeptide derivatives as aminopeptidase N inhibitors
-
Aminopeptidase N (APN/CD13) is one of the essential proteins for tumour invasion, angiogenesis and metastasis as it is over-expressed on the surface of different tumour cells. Based on our previous work that L-isoserine dipeptide derivatives were potent APN inhibitors, we designed and synthesized L-isoserine tripeptide derivatives as APN inhibitors. Among these compounds, one compound 16l (IC50=2.51±0.2 M) showed similar inhibitory effect compared with control compound Bestatin (IC50=6.25±0.4 M) and it could be used as novel lead compound for the APN inhibitors development as anticancer agents in the future.
- Pan, Huili,Yang, Kanghui,Zhang, Jian,Xu, Yingying,Jiang, Yuqi,Yuan, Yumei,Zhang, Xiaopan,Xu, Wenfang
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p. 717 - 726
(2013/07/26)
-
- Direct amidation of amino acid derivatives catalyzed by arylboronic acids: Applications in dipeptide synthesis
-
The direct amidation of amino acid derivatives catalyzed by arylboronic acids has been examined. The reaction was generally slow relative to simple amine-carboxylic acid combinations though proceeded at 65-68 °C generally avoiding racemization. 3,4,5-Trifluorophenylboronic and o-nitrophenylboronic acids were found to be the best catalysts, though for slower dipeptide formations, high catalyst loadings were required and an interesting synergistic catalytic effect between two arylboronic acids was discovered. Arylboronic acids can be used to catalyze the direct amide formation of protected amino acid derivatives. For less reactive amino acids, cooperative catalysis can be used involving two arylboronic acids, one electron-rich and one electron-deficient, at high catalyst loadings to give good conversions at moderate temperatures. Copyright
- Liu, Shouxin,Yang, Yihua,Liu, Xinwei,Ferdousi, Farhana K.,Batsanov, Andrei S.,Whiting, Andrew
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p. 5692 - 5700
(2013/09/12)
-
- Analysis of designed β-hairpin peptides: Molecular conformation and packing in crystals
-
The crystal structures of several designed peptide hairpins have been determined in order to establish features of molecular conformations and modes of aggregation in the crystals. Hairpin formation has been induced using a centrally positioned D/su
- Aravinda, Subrayashastry,Raghavender, Upadhyayula S.,Rai, Rajkishor,Harini, Veldore V.,Shamala, Narayanaswamy,Balaram, Padmanabhan
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p. 4220 - 4231
(2013/07/25)
-
- Biomimetic peptide bond formation in water with aminoacyl phosphate esters
-
Aminoacyl phosphates, biomimetic analogues of aminoacyl adenylates, react efficiently with amino acid esters to form dipeptides with retention of stereochemical integrity. The reactions are selective and occur readily in the presence of nucleophiles other than amino groups on their side chains. Aminoacyl phosphate esters that lack an amino-protecting group are also suitable for peptide bond formation, leading to a simplified overall process.
- Dhiman, Raj S.,Opinska, Liliana Guevara,Kluger, Ronald
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supporting information; experimental part
p. 5645 - 5647
(2011/09/15)
-
- Design, synthesis and primary activity assay of bi- or tri-peptide analogues with the scaffold l-arginine as amino-peptidase N/CD13 inhibitors
-
A series of bi- or tri-peptide analogues with the scaffold l-arginine were designed, synthesized and evaluated for their inhibitory activities against amino-peptidase N (APN) and metalloproteinase-2 (MMP-2). The primary activity assay showed that all the compounds exhibited higher inhibitory activities against APN than MMP-2. Within this series, compounds C6 and C7 (IC50 = 4.2 and 4.3 μM) showed comparable APN inhibitory activities with the positive control bestatin (IC50 = 3.8 μM).
- Mou, Jiajia,Fang, Hao,Liu, Yingzi,Shang, Luqing,Wang, Qiang,Zhang, Lei,Xu, Wenfang
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scheme or table
p. 887 - 895
(2010/05/02)
-
- Design, synthesis, and complementary recognition of β-hairpin peptides stabilized by artificial DNA base-pairing amino acids
-
A novel DNA base-pairing β-hairpin peptide involving intramolecular hydrogen bonds for induction of β-hairpin secondary structure and intermolecular complementary hydrogen bonds between thymine and diaminopyridine for molecular recognition has been synthe
- Isozaki, Katsuhiro,Miki, Kazushi
-
supporting information; experimental part
p. 2947 - 2949
(2010/08/04)
-
- Expanding the peptide β -turn in α γ hybrid sequences: 12 atom hydrogen bonded helical and hairpin turns
-
Hybrid peptide segments containing contiguous a and y amino acid residues can form C 12 hydrogen bonded turns which may be consideredas backbone expanded analogues of C 10 OS-turns) found in aa segments. Exploration of the regular hy
- Chatterjee, Sunanda,Vasudev, Prema G.,Raghothama, Srinivasarao,Ramakrishnan, Chandrasekharan,Shamala, Narayanaswamy,Balaram, Padmanabhan
-
supporting information; experimental part
p. 5956 - 5965
(2009/09/24)
-
- Design and synthesis of a novel class of furan-based molecules as potential 20S proteasome inhibitors
-
A novel class of furan-based compounds as potential 20S proteasome inhibitors have been designed and synthesized, among which nine compounds are peptide derivatives and six molecules are statine peptidomimetics. The C-terminal furanyl moiety was introduced to target molecules as furan-based amino acids. All the compounds were obtained steadily with moderate to high yield. Compound 12 was a selective moderate potent proteasome peptidomimetic inhibitor. It inhibited HepG2 and HL-60 proliferation effectively.
- Fu, Yiqiu,Xu, Bo,Zou, Xiaomin,Ma, Chao,Yang, Xiaoming,Mou, Ke,Fu, Gang,Lue, Yang,Xu, Ping
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p. 1102 - 1106
(2007/10/03)
-
- Synthetic approaches to peptides containing the l-Gln-l-Val-D(S)-Dmt motif
-
The pseudoprolines S-Dmo (5,5-dimethyl-4-oxaproline) and R-Dmt (5,5-dimethyl-4-thiaproline) have been used to study the effects of forcing a fully cis conformation in peptides. Synthesis of peptides containing these (which have the same configuration as l-Pro) is straightforward. However, synthesis of peptides containing S-Dmt is difficult, owing to the rapid cyclisation of l-Aaa-S-Dmt amides and esters to form the corresponding diketopiperazines (DKP); thus the intermediacy of l-Aaa-S-Dmt amides and esters must be avoided in the synthetic sequence. Peptides containing the l-Gln-l-Val-D(S)-Dmt motif are particularly difficult, owing to the insolubility of coupling partners containing Gln. Introduction of Gln as N-Boc-pyroglutamate overcame the latter difficulty and the dipeptide active ester BocPygValOC6F5 coupled in good yield with S-DmtOH. BocPygVal-S- DmtNH(CH2)2C6H4NO2 was converted quantitatively to BocGlnVal-S-DmtNH(CH2)2C6H4NO2 with ammonia, demonstrating the utility of this approach. Two peptide derivatives (CbzSerLysLeuGlnVal-S-DmtNH(CH2)2C6H4NO2 and CbzSerSerLysLeuGlnVal-S- DmtNH(CH2)2C6H4NO2) were assembled, using these new methods of coupling a dipeptide acid active ester with S-DmtOH and introduction of Gln as Pyg, followed by conventional peptide couplings. The presence of the Val caused these peptides to be cleaved very slowly by prostate-specific antigen (PSA) at Leu ↓ Gln, rather than the expected Gln ↓ Val.
- Suaifan, Ghadeer A.R.Y.,Arafat, Tawfiq,Threadgill, Michael D.
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p. 3474 - 3488
(2008/02/05)
-
- The role of terminal tyrosine residues in the formation of tripeptide nanotubes: a crystallographic insight
-
Terminally protected acyclic tripeptides containing tyrosine residues at both termini self-assemble into nanotubes in crystals through various non-covalent interactions including intermolecular hydrogen bonds. The nanotube has an average internal diameter of 5 ? (0.5 nm) and the tubular ensemble is developed through the hydrogen-bonded phenolic-OH side chains of tyrosine (Tyr) residues [Org. Lett. 2004, 6, 4463]. We have synthesized and studied several tripeptides 3-6 to probe the role of tyrosine residues in nanotube structure formation. These peptides either have only one Tyr residue at N- or C-termini or they have one or two terminally located phenylalanine (Phe) residues. These tripeptides failed to form any kind of nanotubular structure in the solid state. Single crystal X-ray diffraction studies of these peptides 3-6 clearly demonstrate that substitution of any one of the terminal Tyr residues in the Boc-Tyr-X-Tyr-OMe (X=Val or Ile) sequence disrupts the formation of the nanotubular structure indicating that the presence of two terminally located Tyr residues is vital for nanotube formation.
- Ray, Sudipta,Drew, Michael G.B.,Das, Apurba Kumar,Banerjee, Arindam
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p. 7274 - 7283
(2007/10/03)
-
- A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenylmethyl chloroformate as a coupling agent
-
The synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc group for Nα-protection and 9-fluorenylmethyl chloroformate (Fmoc-Cl) for the formation of peptide bond is described. The protocol employing Fmoc-Cl as coupling reagent is found to be simple, efficient and rapid. All the intermediate peptides as well as the final protected peptide Boc-Tyr( iBu)-Pro-Phe-Pro-Gly-OMe have been isolated and fully characterized. They have been obtained in good yield and with high purity.
- Babu, V.V. Suresh,Tantry
-
p. 2708 - 2712
(2007/10/03)
-
- N, N′-Carbonyldisaccharin: A new condensing agent for the synthesis of amides, esters and peptides
-
A new, easy to handle and efficient condensing agent N,-N′ -carbonyldisaccharin 2 has been readily synthesised by the reaction of saccharin 1 and trichloromethyl chloroformate in toluene. The condensing agent 2 is demonstrated to be useful for the synthesis of amides, esters and dipeptides under mild conditions in a one-pot procedure.
- Yadav,Dubey, Suman,Singh, Amrish
-
p. 2601 - 2603
(2007/10/03)
-
- β-lactam derivatives as enzyme inhibitors: Derivatives of (E)-2-[(RS)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylidene]propionic acid
-
The 1,4-diaryl disubstituted azetidin-2-one (β-lactam) 1 is transformed into the 3-methylidene derivative (E)-2-[(RS)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-ylidene]propionic acid (3), and then, using the DCC/NHS method reacted with amino acid esters and dipeptide esters forming 3-(peptidyl)-β-lactams 5 and 7. Structures and properties are evaluated mainly by spectroscopic methods and discussed. As molecular modeling experiments might suggest a potential activity as inhibitors of PPE(HLE), a number of selected compounds has been tested in an enzyme assay. But none of them showed any remarkable inhibitory activity. Evaluation of the data was done with the new program EnKinPlot.
- Venz,Otto
-
p. 686 - 690
(2007/10/03)
-
- Differences arising in human neutrophil activation passing from N-formyl to N-acetyl-oligopeptides
-
N-formyl- and N-acetyl-peptides were synthesized and compared in order to understand which features can best elicit biological responses. The behavior of N-formyl-peptides confirms the previously found sequential obligations in the residues, while acetyl-
- Spisani, Susanna,Cavicchioni, Giorgio
-
p. 252 - 259
(2007/10/03)
-
- Synthesis of a new saccharin derivative (BID-SPy) and its utilization as a condensing reagent in the preparation of dipeptides
-
A new saccharin derivative, thiopyridyl-benzisothiazole 1,1-dioxide (BID-SPy, 2), has been prepared by the reaction of BID-Cl (1) and 2-mercaptopyridine, and utilized as a coupling reagent in the synthesis of amides and N-protected dipeptides.
- Ahmed, A,Akhter, H
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p. 564 - 565
(2007/10/02)
-
- Facile Conversions of Carboxylic Acids into Amides, Esters, and Thioesters Using 1,1'-Oxalyldiimidazole and 1,1'-Oxalyldi(1,2,4-triazole)
-
Aliphatic, aromatic, and heteroaromatic carboxylic acids react with 1,1'-oxalyldiimidazole (1) or 1,1'-oxalyldi(1,2,4-triazole) (2) in acetonitrile for 40 min at 40 degC to give the corresponding 1-acylazole intermediates (11), which promptly undergo aminolysis and alcoholysis to form amides (13) including dipeptides (14), esters (16), and thioesters (19).These findings show that both 1 and 2 can be utilized as condensing reagents for the synthesis of carboxylic acid derivatives.Keywords --- 1,1'-oxalyldiimidazole; 1,1'-oxalyldi(1,2,4-triazole); 1,1'-carbonyldiimidazole; 1-acylazole; condensing reagent; amidation; esterification; dipeptide; aminolysis; alcoholysis
- Kitagawa, Tokujiro,Kuroda, Hiroko,Sasaki, Hideaki,Kawasaki, Koichi
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p. 4294 - 4301
(2007/10/02)
-
- 3,3'-(Phenylphosphinylidene)bis and 3,3'-(Phenylphosphinylidene)bis. New Activating Agents
-
New activating agents, 3,3'-(phenylphophinylidene)bis (4) and 3,3'-(phenylphosphinylidene)bis (5), were readily prepared by the reaction of phenylphosphonic dichloride (3) with 2(3H)-benzoxazolone (1) and 2(3H)-benzothiazolone (2) respectively in the presence of triethylamine at room temperature.The new activating agents 4 and 5 were found to be useful for the preparation of amides, esters, and dipeptides under mild conditions.Furthemore, the direct polycondensation of isophthalic acid with aromatic diamines using the activating agent 4 in the presence of pyridine proceeded fast at room temperature to produce polyamides with inherent viscosities up to 0.80 dL/g.
- Ueda, Mitsuru,Mochizuki, Amane,Hiratsuka, Ichiro,Oikawa, Hideaki
-
p. 3291 - 3297
(2007/10/02)
-
- 1,2-Benzisoxazol-3-yl Diphenyl Phosphate: A New, Reactive Activating Agent for the Synthesis of Amides, Esters, and Peptides via Condensation
-
A new activating agent for condensations, 1,2-benzisoxazol-3-yl diphenyl phosphate (1), was readily prepared in high yield by the reaction of 1,2-benzisoxazol-3-ol (2) with diphenyl phosphorochloridate (3) in the presence of triethylamine in benzene.The reaction of the carboxylic acids with the amines in the presence of 1 was investigated by two procedures, a two-step method and a one-step procedure.Both methods gave the corresponding amides and esters in high yields under mild conditions, but the one-step procedure was found to be superior to the two-step procedure because of its simplicity and speed.Furthermore, the activating agent 1 was shown to be a useful peptide forming reagent.
- Ueda, Mitsuru,Oikawa, Hideaki
-
p. 760 - 763
(2007/10/02)
-
- THE SYNTHESIS OF AMIDES, ESTERS, AND THIOESTERS
-
Diethyl 2-(3-oxo-2,3-dihydro-1,2-benzisosulfonazolyl)phosphonate is a highly reactive condensing agent, which provides good yield route to amides, esters, and thioesters from a variety of amines, active hydroxylamines, and thiols and acids.
- Miyake, Muneharu,Kirisawa, Makoto,Tokutake, Norio
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p. 123 - 126
(2007/10/02)
-
- 2(3H)-BENZOXAZOLETHIONE.
-
A new condensing agent, N,N prime -carbonyldi left bracket 2(3H)-benzoxazolethione right bracket , was readily prepared by the reaction of 2-benzoxazolethiol and trichloromethyl chloroformate in benzene. The condensing agent is shown to be useful for the preparation of amides, esters, and dipeptides under mild conditions. A successful polyamide synthesis by the polycondensation of isophthalic acid with diamines using the condensing agent is also described.
- Ueda,Kawaharasaki,Imai
-
-
- A New and Effective Synthetic Method for the Preparation of the Esters, Peptides, and Lactones Using 3-(5-Nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1-Dioxide. Synthesis of (+/-)-E-Dodecen-11-olide, Recifeiolide
-
3-(5-nitro-2-oxo-1,2-dihydro-1-pyridyl)-1,2-benzisothiazole 1,1-dioxide (BID-NPy), readily prepared from 3-chloro-1,2-benzisothiazole 1,1-dioxide and 5-nitro-2-pyridone, proved to be a very useful condensing reagent.A variety of esters, dipeptides, and lactones were obtained in excellent yields.Furthemore, BID-NPy was successfully employed for the lactonization step in a new synthesis of a naturally occuring (+/-)-(E)-8-dodecen-11-olide, recifeiolide.
- Ahmed, Alauddin,Taniguchi, Nagahiro,Fukuda, Hirohiko,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
-
p. 781 - 786
(2007/10/02)
-
- 1,2-BENZISOXAZOL-3(2H)-ONE.
-
A new condensing agent, N,N prime -carbonyldi left bracket 1,2-benzisoxazol-3(2H)-one right bracket (6), was readily prepared by the reaction of 1,2-benzisoxazol-3-ol and trichloromethyl chloroformate in toluene. The condensing agent 6 was shown to be very useful for the preparation of amides, esters, and dipeptides under mild conditions. A successful polyamide synthesis by one-pot polycondensation of isophthalic acid with diamines using 6 is also described.
- Ueda,Oikawa,Kawaharasaki,Imai
-
p. 2485 - 2489
(2007/10/02)
-
- 3-(5-NITRO-2-PYRIDON-1-YL)-1,2-BENZOISOTHIAZOLE 1,1-DIOXIDE (BID-NPy) AS A NEW EFFECTIVE CONDENSING REAGENT
-
3-(5-Nitro-2-pyridon-1-yl)-1,2-benzoisothiazole 1,1-dioxide (BID-NPy) was found to be a useful condensing reagent.Various dipeptides and esters were prepared in good yields using this reagent.
- Ahmed, Alauddin,Fukuda, Hirohiko,Inomata, Katsuhiko,Kotake, Hiroshi
-
p. 1161 - 1164
(2007/10/02)
-
- Cyclic esters of 3,4-dihydroxy-thiophene-1,1-dioxide compounds and 3,4-dihydroxy-cyclopentadienone compounds
-
Cyclic esters of 3,4-dihydroxy-thiophene-1,1-dioxide and of the corresponding cyclopentadienone compound, and their manufacture. The compounds can be used as "solid forms" of phosgene, thiophosgene or oxalyl chloride, or as acyl transfer agents.
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