Synthesis of 1,2-Diazepines by the Bischler-Napieralski Reaction

被引:4
作者
Muratov, A. V. [1 ]
Grebenyuk, S. A. [1 ]
Eresko, A. B. [1 ]
机构
[1] Litvinenko Inst Phys Organ & Coal Chem, Ul R Lyuksemburg 70, UA-83114 Donetsk, Ukraine
关键词
AMPAR ANTAGONISTS; RECEPTOR; 2,3-BENZODIAZEPINES;
D O I
10.1134/S1070428018060064
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy has been proposed for the synthesis of 5H-[1]benzofuro[2,3-d][1,2]diazepines containing two aryl substituents in the diazepine fragment. The key stage of the synthesis is intramolecular cyclization of the corresponding hydrazides under the Bischler-Napieralski reaction conditions.
引用
收藏
页码:861 / 866
页数:6
相关论文
共 20 条
[1]   Search for noncompetitive 2-amino-3(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid receptor (AMPAR) antagonists: Synthesis, pharmacological properties, and computational studies [J].
Chimirri, A ;
De Sarro, G ;
Quartarone, S ;
Barreca, ML ;
Caruso, R ;
De Luca, L ;
Gitto, R .
PURE AND APPLIED CHEMISTRY, 2004, 76 (05) :931-939
[2]   Bischler-Napieralski cyclocondensation in the synthesis of new 11H-pyrimido[4,5-b][1,4]benzodiazepines [J].
Cobo, Justo ;
Nogueras, Manuel ;
Low, John N. ;
Rodriguez, Ricaurte .
TETRAHEDRON LETTERS, 2008, 49 (51) :7271-7273
[3]   7,8-methylenedioxy-4H-2,3-benzodiazepin-4-ones as novel AMPA receptor antagonists [J].
De Sarro, A ;
De Sarro, G ;
Gitto, R ;
Grasso, S ;
Micale, N ;
Quartarone, S ;
Zappala, M .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (08) :971-976
[4]   On the synthesis of pyrrolobenzo[b]thieno[1,4]diazepines [J].
El-Kashef, Hussein ;
Rathelot, Pascal ;
Vanelle, Patrice ;
Rault, Sylvain .
MONATSHEFTE FUR CHEMIE, 2007, 138 (05) :469-476
[5]   CONDENSED DIAZEPINES. SYNTHESIS OF 1-ARYL-3,5-DIHYDRO-4H-1-BENZOFURO-[2,3-d][1,2]DIAZEPIN-4-ONES [J].
Eresko, A. B. ;
Tolkunov, V. S. ;
Tolkunov, S. V. .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (09) :1127-1132
[6]   Simple and efficient preparation of 3-substituted 6-(4-chlorophenyl)-9-methyl-12H-[1]benzofuro[3,2-e][1,2,4]triazolo[4,3-b][1,2]diazepines via a silylation-amination reaction [J].
Eresko, Alexander ;
Tolkunov, Valerij ;
Tolkunov, Sergej .
MONATSHEFTE FUR CHEMIE, 2011, 142 (09) :931-934
[7]   Development of novel N-3-bromoisoxazolin-5-yl substituted 2,3-benzodiazepines as noncompetitive AMPAR antagonists [J].
Espahbodinia, Milad ;
Ettari, Roberta ;
Wen, Wei ;
Wu, Andrew ;
Shen, Yu-Chuan ;
Niu, Li ;
Grasso, Silvana ;
Zappala, Maria .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (14) :3631-3637
[8]   Synthesis of novel tricyclic pyrimido[4,5-b][1,4]benzothiazepines via Bischler-Napieralski-type reactions [J].
Fu, RZ ;
Xu, XX ;
Dang, Q ;
Bai, X .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (26) :10810-10816
[9]   Modern approaches to the design of memory and cognitive enhancers based on AMPA receptor ligands [J].
Grigoriev, V. V. ;
Proshin, A. N. ;
Kinzirsky, A. S. ;
Bachurin, S. O. .
RUSSIAN CHEMICAL REVIEWS, 2009, 78 (05) :485-494
[10]   AMPA receptor modulators as cognitive enhancers [J].
Lynch, G .
CURRENT OPINION IN PHARMACOLOGY, 2004, 4 (01) :4-11