1-Aryl-4-(2-oxoalkylsulfanyl)-2,3(5H)-benzodiazepines: synthesis and thiophene ring annulation to 1,2-diazepine core

被引：0

作者：

Bohdan, Natalia M. ^{[1
]}

Stepanova, Diana S. ^{[1
]}

Suikov, Serhii Yu. ^{[1
]}

Popov, Vadim Yu. ^{[2
]}

Ishkov, Yuri V. ^{[3
]}

Bohza, Serhii L. ^{[1
,2
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, 5 Akademika Kukharya St, UA-02094 Kiev, Ukraine

[2] Natl Acad Sci Ukraine, L M Litvinenko Inst Phys Organ Chem & Coal Chem, 50 Kharkivske Rd, UA-02155 Kiev, Ukraine

[3] Odesa I I Mechnikov Natl Univ, 2 Dvoryanskaya St, UA-65082 Odesa, Ukraine

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2023年 / 59卷 / 6-7期

关键词：

2,3-benzodiazepine; thione; alkylation; cyclization; NMR analysis; synthesis; AMPA RECEPTOR ANTAGONISTS; ROUTE;

D O I：

10.1007/s10593-023-03223-w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1-Aryl-2-[(1-aryl-5H-2,3-benzodiazepin-4-yl)sulfanyl]ethanones were obtained by the alkylation of 1-aryl-2,3-benzodiazepine-4(3H,5H)-thiones with 1-aryl-2-bromoethanones. A reaction for the annulation of the thiophene core to the 1,2-diazepine ring as a result of intramolecular cyclization involving a 4-aroylmethylsulfanyl substituent and C(4)-C(5) bond of diazepine was developed. Derivatives of a new thieno[2,3-d][2,3]benzodiazepine heterocyclic system were synthesized.

引用

页码：508 / 511

页数：4

共 50 条

[1] 1-Aryl-4-(2-oxoalkylsulfanyl)-2,3(5H)-benzodiazepines: synthesis and thiophene ring annulation to 1,2-diazepine core
Natalia M. Bohdan
Diana S. Stepanova
Serhii Yu. Suikov
Vadim Yu. Popov
Yuri V. Ishkov
Serhii L. Bohza
Chemistry of Heterocyclic Compounds, 2023, 59 : 508 - 511
[2] STRUCTURE OF A 1,2-DIAZEPINE ANALOG OF A DIAZA[24](1,2,4,5)CYCLOPHANE
HANSON, AW
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1986, 42 : 1458 - 1460
[3] Synthesis of a new pyrrolo[1,3]diazepine: 4H-pyrrolo[1,2-a]thieno[2,3-e][1,3]diazepine
Daich, A
Ohier, P
Decroix, B
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (06) : 1731 - 1734
[4] 4-Aryl-1-hydrazino-5H-2,3-benzodiazepine and 1-aryl-4-hydrazino-5H-2,3-benzodiazepine in the synthesis of condensed [1,2]diazepines
Kharaneko, O. I.
Popov, V. Yu.
Bogza, S. L.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (02) : 317 - 324
[5] 4-Aryl-1-hydrazino-5H-2,3-benzodiazepine and 1-aryl-4-hydrazino-5H-2,3-benzodiazepine in the synthesis of condensed [1,2]diazepines
O. I. Kharaneko
V. Yu. Popov
S. L. Bogza
Chemistry of Heterocyclic Compounds, 2013, 49 : 317 - 324
[6] 1,2,3,4-TETRAHYDRO-1,2-DIAZEPINE DERIVATIVES - SYNTHESIS AND EVALUATION OF ANTILEUKEMIC ACTIVITY
DALPIAZ, V
CICIANI, G
FARMACO-EDIZIONE SCIENTIFICA, 1988, 43 (11): : 943 - 949
[7] [2+4] AND [6+4] TYPE CYCLOADDITION REACTIONS OF 1-ETHOXYCARBONYL-1H-AZEPINE AND 1-ETHOXYCARBONYL-1H-1,2-DIAZEPINE WITH 3,4,5,6-TETRACHLORO-1,2-BENZOQUINONE
SAITO, K
MUKAI, T
IIDA, S
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (08) : 2485 - 2488
[8] Synthesis of 4-Aryl-2(5H)-furanones by Gold(I)-Catalyzed Intramolecular Annulation
Sun, Haifeng
Huang, He
Zhang, Dengyou
Feng, Enguang
Qian, Wangke
Zhang, Lei
Chen, Kaixian
Liu, Hong
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (09) : 1413 - 1419
[9] CYCLOADDITION REACTIONS OF 1-ETHOXYCARBONYL-H-1-AZEPINE AND "1-ETHOXY-CARBONYL-H-1-1,2-DIAZEPINE WITH 3,4,5,6-TETRACHLORO-1,2-BENZOQUINONE
SAITO, K
IIDA, S
MUKAI, T
HETEROCYCLES, 1982, 19 (07) : 1197 - 1202
[10] Mucochloric acid:: A useful synthon for the selective synthesis of 4-aryl-3chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidenel-3-chloro-2(5H)furanones and 3,4-diaryl-2(5H)-furanones
Bellina, F
Anselmi, C
Martina, F
Rossi, R
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (12) : 2290 - 2302

← 1 2 3 4 5 →