- Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C-O Coupling
-
A convenient approach to assemble 1,2,3-triazole-fused 4 H -3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C-O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C-I bond was achieved by the use of Na 2CO 3in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.
- Tatevosyan, Stepan S.,Kotovshchikov, Yury N.,Latyshev, Gennadij V.,Lukashev, Nikolay V.,Beletskaya, Irina P.
-
supporting information
p. 369 - 377
(2021/10/21)
-
- Ruthenium complexes of phosphine-amide based ligands as efficient catalysts for transfer hydrogenation reactions
-
This work presents three mononuclear Ru(ii) complexes of tridentate phosphine-carboxamide based ligands providing a NNP coordination environment. The octahedral Ru(ii) ion shows additional coordination with co-ligands; CO, Cl and CH3OH. All three Ru(ii) complexes were thoroughly characterized including their crystal structures. These Ru(ii) complexes were utilized as catalysts for the transfer hydrogenation of assorted carbonyl compounds, including some challenging biologically relevant substrates, using isopropanol as the hydrogen source. The binding studies illustrated the coordination of the isopropoxide ion by replacing a Ru-ligated chloride ion followed by the generation of the Ru-H intermediate that was isolated and characterized and was found to be involved in the catalysis.
- Yadav, Samanta,Vijayan, Paranthaman,Yadav, Sunil,Gupta, Rajeev
-
p. 3269 - 3279
(2021/03/16)
-
- An efficient iron-promoted synthesis of 6H-indolo[2,3- b] quinolines and neocryptolepine derivatives
-
A facile and practical method for the preparation of 6H-indolo[2,3-b]quinolines and neocryptolepines was developed under the promotion of the easily available ferric trichloride, affording the desired products with moderate to good yields.
- Yan, Zicong,Wan, Changfeng,Wan, Jianyong,Wang, Zhiyong
-
supporting information
p. 4405 - 4408
(2016/06/06)
-
- A simple route to polysubstituted indoles exploiting azide induced furan ring opening
-
A straightforward, efficient indole synthesis based on thermolysis of 2-(2-azidobenzyl)furans with attack of the formed nitrene moiety onto the ipso position of furan ring has been developed. The cyclization is accompanied by furan ring opening and affords indoles with a 2-acylvinyl substituent suitable for further modifications.
- Abaev, Vladimir T.,Plieva, Anastasiya T.,Chalikidi, Petrakis N.,Uchuskin, Maxim G.,Trushkov, Igor V.,Butin, Alexander V.
-
supporting information
p. 4150 - 4153
(2014/09/30)
-
- Metal-free intramolecular oxidative decarboxylative amination of primary α-amino acids with product selectivity
-
A novel metal-free intramolecular oxidative decarboxylative coupling of primary α-amino acids with 2-aminobenzoketones under mild and neutral conditions was developed. Different quinazolines can be selectively obtained by various oxidants.
- Yan, Yizhe,Wang, Zhiyong
-
p. 9513 - 9515
(2011/10/01)
-
- Discovery of a new 2-aminobenzhydrol template for highly potent squalene synthase inhibitors
-
To obtain small and efficient squalene synthase inhibitors, a flexible 2-aminobenzhydrol open form structure was designed and showed potent inhibitory activity comparable to 4,1-benzoxazepin compounds. Further chemical modification led to the discovery of a novel template with a strong squalene synthase inhibitory activity, and its basic structure-activity relationship was revealed. The X-ray crystallographic data of compound 12 bound to the active site of squalene synthase provided an important insight into the binding mode of this alternative template that formed 11-membered ring conformations with an intramolecular hydrogen bond.
- Ichikawa, Masanori,Yokomizo, Aki,Itoh, Masao,Sugita, Kazuyuki,Usui, Hiroyuki,Shimizu, Hironari,Suzuki, Makoto,Terayama, Koji,Kanda, Akira
-
scheme or table
p. 1930 - 1949
(2011/05/03)
-
- A simple and efficient approach to the synthesis of 2-phenylquinazolines via sp3 C-H functionalization
-
(Figure presented) A facile and novel approach to the synthesis of 2-phenylquinazolines was developed via a tandem reaction following sp 3 C-H functionalization. Twenty-five examples of 2-phenylquinazolines were obtained from easily available 2-aminobenzophenones and benzylic amines with good to excellent yields.
- Zhang, Jintang,Zhu, Dapeng,Yu, Chenmin,Wan, Changfeng,Wang, Zhiyong
-
supporting information; experimental part
p. 2841 - 2843
(2010/09/04)
-
- A novel and efficient methodology for the construction of quinazolines based on supported copper oxide nanoparticles
-
A series of quinazolines were synthesized from 2-aminobenzophenones and benzylic amines in good to excellent yields by employing a new heterogeneous catalyst based on the copper oxide nanoparticles supported on kaolin.
- Zhang, Jintang,Yu, Chenmin,Wang, Sujing,Wan, Changfeng,Wang, Zhiyong
-
supporting information; experimental part
p. 5244 - 5246
(2010/09/05)
-
- An enantiopure galactose oxidase model: synthesis of chiral amino alcohols through oxidative kinetic resolution catalyzed by a chiral copper complex
-
An enantiopure galactose oxidase (GO) enzyme model has been synthesized from readily available (R)-BINAM and Cu(OTf)2, and the enantiopure GO model has been effectively used in situ as an efficient chiral catalyst for the synthesis of chiral amino alcohols through oxidative kinetic resolution (OKR), where molecular oxygen is used as the sole oxidant. Under the proposed catalytic conditions, both ortho- and para-substituted amino alcohols were resolved with good to excellent enantiomeric excesses through oxidative kinetic resolution.
- Mannam, Sreedevi,Sekar, Govindasamy
-
experimental part
p. 497 - 502
(2009/07/18)
-
- A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine
-
(Chemical Equation Presented) The reaction of substituted (2-aminobenzyl)triphenylphosphonium bromides with aromatic aldehydes or α,β-unsaturated aldehydes constitutes a new synthesis of 2,3-disubstitued indoles in high yields. The adduct from 4-oxo-3,4- dihydroquinazoline-2-carbaldehyde was an advanced intermediate in the synthesis of several rutaecarpines.
- Kraus, George A.,Guo, Haitao
-
scheme or table
p. 5337 - 5341
(2009/11/30)
-
- Cascade synthesis of 3-quinolinecarboxylic ester via benzylation/ propargylation-cyclization
-
(Chemical Equation Presented) Reactions of 2-amino-aryl alcohols with β-ketoesters catalyzed by a catalytic amout of FeCl3 via tandem benzylation-cyclization produce the corresponding 3-quinolinecarboxylic esters in good to high yields. Extending this methodology to propargylation- cyclization, 2-nitrophenyl propargyl alcohols with β-ketoesters catalyzed by FeCl3 and SnCl2 also produce the 4-alkyne-3- quinolinecarboxylic esters. The mechanistic details of this benzylation/ propargylation and cyclization cascade process are also discussed.
- Fan, Jinmin,Wan, Changfeng,Sun, Gaojun,Wang, Zhiyong
-
supporting information; experimental part
p. 8608 - 8611
(2009/04/04)
-
- Synthesis of the antitumoural agent batracylin and related isoindolo[1,2-b]quinazolin-12(10H)-ones
-
The synthesis of batracylin and related isoindolo[1,2-b]quinazolin-12-ones from easily accessible o-acylanilines is reported. The preparation of these tetracyclic compounds through a Mitsunobu reaction followed by spontaneous cyclodehydration shows the ability of this methodology to afford good yields of a wide variety of diversely 7, 8, 9, 10-substituted isoindoloquinazolinones in two steps.
- Martínez-Viturro, Carlos M.,Domínguez, Domingo
-
p. 1023 - 1026
(2008/02/04)
-
- 5-Aryl-imidazo[2,1-c][1,4]benzodiazepine derivatives as tricyclic constrained analogues of diazepam and Ro5-4864. Synthesis and binding properties at peripheral and central benzodiazepine receptors
-
Four series of 5-aryl-imidazo[2,1-c][1,4]benzodiazepine derivatives 1a-f, 2a-f, 3a-f, and 4a-f were synthesized and tested for their affinity at both the peripheral and central benzodiazepine receptors. Among the four series, only N-10 and C-11 sites were changed, mainly [N(CH3)-CO], [N-CH], [NH-CO], [NH-CH2], and in each series the halogen site was varied at the positions C-7, C-2′, and C-4′. In particular, 10-methyl-benzodiazepinones 1a and 1b were designed as tricyclic constrained analogues of diazepam and Ro5-4864. All the tested compounds did not show significant binding activity at central benzodiazepine receptors, but relatively good PBzR binding affinities were found for 10-methyl-benzodiazepinone 1c and benzodiazepines 2b, c. Benzodiazepinones 3a-f were prepared by cyclization with 1,1′-carbonyldiimidazole of the corresponding 2-(aryl-imidazol-1-yl- methyl)-arylamines, obtained from the suitable (2-amino-aryl)-aryl-methanols with 1,1′-carbonyldiimidazole in different conditions. N-Alkylation of 3a-f to 1a-f was achieved using dimethylformamide-dimethylacetal. Reduction of 3a-f to 4a-f was accomplished with lithium aluminum hydride or borane and oxidation of 4a-f to 2a-f was performed with manganese (IV) oxide.
- Rizzetto, Elisa,Castellano,Florio,Vadori,Stefancich
-
p. 505 - 510
(2007/10/03)
-
- ISOQUINOLINE-5-SULFONIC ACID AMIDES AS INHIBITORS OF AKT (PROTEIN KINASE B)
-
The present invention relates to compounds Formula (I): as inhibitors of AKT activity, which are useful for the treatment of susceptible neoplasms and viral infections.
- -
-
-
- Pinacol Formation and Reduction of Aromatic Carbonyls with Magnesium-Methanol at Ambient Temperature
-
A simple and inexpensive procedure for the pinacol formation of aromatic aldehydes and reduction of aromatic ketones to the corresponding alcohols with magnesium in dry methanol at ambient temperature is reported. The pinacol formation and reduction are proposed to be proceeding by SET from magnesium.
- Khurana, Jitender M.,Bansal, Geeti,Kukreja, Gagan,Pandey, Ravi R.
-
p. 1365 - 1371
(2007/10/03)
-
- Novel 4,1-benzoxazepine derivatives with potent squalene synthase inhibitory activities
-
A series of (3,5-trans)-2-oxo-5-phenyl-1,2,3,5-tetrahydro-4,1-benzoxazepine derivatives were synthesized and evaluated for squalene synthase inhibitory and cholesterol biosynthesis inhibitory activities. Through modification of substituents of the lead compounds 1a and 1b, it was found that 4,1-benzoxazepine-3-acetic acid derivatives with isobutyl and neopentyl groups at the 1-position, the chloro atom at the 7-position, and the chloro and methoxy groups at the 2'-position on the 5-phenyl ring, had potent squalene synthase inhibitory activity. Among such compounds, the 5-(2,3-dimethoxyphenyl) derivative 2t exhibited potent inhibition of cholesterol biosynthesis in HepG2 cells. As a result of optical resolution study of 2t, the absolute stereochemistry required for inibitory activity was determined to be 3R,5S. In vivo study showed that the sodium salt of (3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-neopentyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-aceitc acid 20 effectively reduced plasma cholesterol in marmosets. Copyright
- Miki, Takashi,Kori, Masakuni,Mabuchi, Hiroshi,Banno, Hiroshi,Tozawa, Ryu-ichi,Nakamura, Masahira,Itokawa, Shigekazu,Sugiyama, Yasuo,Yukimasa, Hidefumi
-
p. 401 - 414
(2007/10/03)
-
- Rapid reduction of carbonyls with nickel boride at ambient utemperature
-
Carbonyl compounds have been reported to undergo rapid reduction with nickel boride generated in situ from anhyd. nickel chloride and sodium borohydride in THF at ambient temperature to the corresponding alcohols in high yields.
- Khurana,Chauhan
-
p. 3485 - 3489
(2007/10/03)
-
- Ureas in Organic Synthesis. XII. Syntesis of 2-Amino-5-chlorobenzhydrylureas and Their Heterocyclization
-
A synthetic method was developed for hard-to-get biologically active 2-amino-5-chlorobenzhydrylureas based on reaction of the corresponding benzhydrols with urea in sulfuric acid. The 2-amino-5-chlorobenzhydrylureas were shown to easily undergo on heating cyclization to 1-R-1,2,3,4-tetrahydro-4-phenyl-chloroquinazolin-2-ones.
- Bakibaev,Shtrykova,Vostretsov
-
p. 457 - 459
(2007/10/03)
-
- Synthesis of chiral alcohols by asymmetric reductions of various ketones including α-aminophenones
-
LiAlH4 previously treated with 2.5 equiv. of (S)-(+) or (R)-(-)-2-(2-isoindolinyl)butan-1-ol 1 reduced the six α-aminophenones 4-9 into the corresponding optically active β-aminoalcohols 10-15 whose ee's were in the range of 40-97% after chroma
- Brown, Eric,Leze, Antoine,Touet, Joel
-
p. 2029 - 2040
(2007/10/03)
-
- Pinacolization and reduction of aromatic carbonyls with aluminium-KOH
-
A simple and rapid procedure for the pinacolization of aromatic aldehydes and reduction of hindered ketones with inexpensive aluminium and KOH in methanol at ambient temperature is reported. The pinacolization and reduction are proposed to be proceeding via single electron transfer from aluminium. Copyright 1996 by the Royal Society of Chemistry.
- Khurana, Jitender M.,Sehgal, Arti,Gogia, Amita,Manian, Aparna,Maikap, Golak C.
-
p. 2213 - 2215
(2007/10/03)
-
- Asymmetric reduction of 2-aminobenzophenone using yeast, Rhodosporidium toruloides
-
(±)-N-Isonicotinoyl-2-amino-5-chlorobenzhydrol (1) is a rice plant growth regulator which shortens the second leaf sheaths. One of the enantiomers, (S)-1, was obtained by microbiological asymmetric reduction of 2-amino-5-chlorobenzophenone using Rhodospor
- Kato,Sasahara,Ochi,Akita,Oishi
-
p. 2498 - 2501
(2007/10/02)
-
- AMINOHALOBORANE IN ORGANIC SYNTHESIS. VIII. A ONE-STEP SYNTHESIS OF 2-AMINOBENZHYDROLS FROM ANILINES
-
2-Aminobenzhydrols were obtained regiospecifically from anilines and benzaldehydes with the aid of phenyldichloroborane and triethylamine via N-anilinophenylchloroborane.
- Toyoda, Tatsuo,Sasakura, Kazuyuki,Sugasawa, Tsutomu
-
p. 173 - 176
(2007/10/02)
-