Intramolecular amidation:: synthesis of novel imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b][1,3]thiazole fused diazepinones

被引：34

作者：

Kolavi, G ^{[1
]}

Hegde, V ^{[1
]}

Khazi, IA ^{[1
]}

机构：

[1] Karnatak Univ, Dept Chem, Dharwad 580003, Karnataka, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 16期

关键词：

thiadiazole; imidazo[2,1-b][1,3,4]thiadiazole; intramolecular amidation; diazepinone;

D O I：

10.1016/j.tetlet.2006.02.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel heterocyclic systems 2-alkyl/aryl-9-(2-hydroxybenzylidene)-7,9-dihydro-8H-[1,3,4]thiadiazolo[2',3':2,3]imidazo[4,5-( [1,2]diazepin-8-one and 9-(2-hydroxy-benzylideile)-3,3-dimethyl-3,4,7,9-tetrahydro-2H-11-thia4b,6,7,10-tetriazaindeno[1,2-a]azulene-1,8-dione are synthesized via an intramolecular annidation reaction. An interesting ring opening and cyclization of 2-alkyl/aryl-6-(2-oxo-2H-chromen-3-yl)imidazo[2, 1-b][1,3,4]thiadiazole-5-carbaldehydc and 6,6-dimethyl-8-oxo-2-(2-oxo-2H-chromen-3-yl)-5,6,7,8-tetrahydromidazo[2,1-b][1,3]benzothiazole-3-carbaldehyde are discussed. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：2811 / 2814

页数：4

共 4 条

[1] Potential antitumor agents. Part 29: Synthesis and potential coanthracyclinic activity of imidazo[2,1-b]thiazole guanylhydrazones [J].

Andreani, A ;

Leoni, A ;

Locatelli, A ;

Morigi, R ;

Rambaldi, M ;

Recanatini, M ;

Garaliene, V .

BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (09) :2359-2366

[2] Potential antitumor agents.: 37.: Synthesis and antitumor activity of guanylhydrazones from imidazo[2,1-b]thiazoles and from the new heterocyclic system thiazolo[2′,3′:2,3]imidazo [4,5-c]quinoline [J].

Andreani, A ;

Granaiola, M ;

Leoni, A ;

Locatelli, A ;

Morigi, R ;

Rambaldi, M ;

Lenaz, G ;

Fato, R ;

Bergamini, C ;

Farruggia, G .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (08) :3085-3089

[3] Synthesis and evaluation of pharmacological properties of novel annelated 2,3-benzodiazepine derivatives [J].

Gitto, R ;

Orlando, V ;

Quartarone, S ;

De Sarro, G ;

De Sarro, A ;

Russo, E ;

Ferreri, G ;

Chimirri, A .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (17) :3758-3761

[4] NOVEL NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE-TRANSCRIPTASE .1. TRICYCLIC PYRIDOBENZODIAZEPINONES AND DIPYRIDODIAZEPINONES [J].

HARGRAVE, KD ;

PROUDFOOT, JR ;

GROZINGER, KG ;

CULLEN, E ;

KAPADIA, SR ;

PATEL, UR ;

FUCHS, VU ;

MAULDIN, SC ;

VITOUS, J ;

BEHNKE, ML ;

KLUNDER, JM ;

PAL, K ;

SKILES, JW ;

MCNEIL, DW ;

ROSE, JM ;

CHOW, GC ;

SKOOG, MT ;

WU, JC ;

SCHMIDT, G ;

ENGEL, WW ;

EBERLEIN, WG ;

SABOE, TD ;

CAMPBELL, SJ ;

ROSENTHAL, AS ;

ADAMS, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (07) :2231-2241

← 1 →