Atom-economical isocyanide-based multicomponent synthesis of 2,5-dioxopyrrolidines, spirobenzothiazinechromans and 1,5-benzothiazepines

被引：18

作者：

Akbarzadeh, Roya ^{[1
]}

Amanpour, Tayebeh ^{[1
]}

Khavasi, Hamid Reza ^{[1
]}

Bazgir, Ayoob ^{[1
]}

机构：

[1] Shahid Beheshti Univ, Dept Chem, Tehran 1983963113, Iran

来源：

TETRAHEDRON | 2014年 / 70卷 / 02期

基金：

美国国家科学基金会;

关键词：

Isocyanide; Dioxopyrrolidine; Spirobenzothiazine-2,3 '-chroman; Benzothiazepines; GLYCOSIDASE INHIBITORS; ANTIMICROBIAL ACTIVITY; NATURAL OCCURRENCE; DERIVATIVES; COMBINATORIAL;

D O I：

10.1016/j.tet.2013.12.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of new pharmaceutically relevant dioxopyrrolidines, spirobenzo thiazine-2,3'chromans, and benzothiazepines via isocyanide-based multicomponent condensation reactions at room temperature is reported. This synthesis serves as a nice addition to group-assistant-purification (GAP) chemistry in which purification via chromatography and recrystallization can be avoided, and the pure products are obtained simply by washing the crude products with 95% ethanol. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：169 / 175

页数：7

共 35 条

[1]

[Anonymous], X STEP32 VERS 1 07B

[2] Naturally occurring iminosugars and related compounds: Structure, distribution, and biological activity [J].

Asano, N .

CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2003, 3 (05) :471-484

[3] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].

Asano, N ;

Nash, RJ ;

Molyneux, RJ ;

Fleet, GWJ .

TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680

[4] Design and synthesis of pyrimido[4,5-b][1,4]benzothiazine derivatives, as potent 15-lipoxygenase inhibitors [J].

Bakavoli, M. ;

Nikpour, M. ;

Rahimizadeh, M. ;

Saberi, M. R. ;

Sadeghian, H. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) :2120-2126

[5] Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs [J].

Barazarte, Arthur ;

Camacho, Jose ;

Dominguez, Jose ;

Lobo, Gricela ;

Gamboa, Neira ;

Rodrigues, Juan ;

Capparelli, Mario V. ;

Alvarez-Larena, Angel ;

Andujar, Sebastian ;

Enriz, Daniel ;

Charris, Jaime .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (07) :3661-3674

[6] 1,4-BENZOTHIAZINES, DIHYDRO-1,4-BENZOTHIAZINES, AND RELATED-COMPOUNDS [J].

BROWN, C ;

DAVIDSON, RM .

ADVANCES IN HETEROCYCLIC CHEMISTRY, 1985, 38 :135-176

[7] PYRROLO[2,1-C][1,4] BENZOTHIAZINES - SYNTHESIS, STRUCTURE-ACTIVITY-RELATIONSHIPS, MOLECULAR MODELING STUDIES, AND CARDIOVASCULAR ACTIVITY [J].

CAMPIANI, G ;

GAROFALO, A ;

FIORINI, I ;

BETTA, M ;

NACCI, V ;

TAFI, A ;

CHIARINI, A ;

BUDRIESI, R ;

BRUNI, G ;

ROMEO, MR .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (22) :4393-4410

[8] Synthesis and anti-inflammatory structure-activity relationships of thiazine-quinoline-quinones: Inhibitors of the neutrophil respiratory burst in a model of acute gouty arthritis [J].

Chia, Elizabeth W. ;

Pearce, A. Norrie ;

Berridge, Michael V. ;

Larsen, Lesley ;

Perry, Nigel B. ;

Sansom, Catherine E. ;

Godfrey, Colette A. ;

Hanton, Lyall R. ;

Lu, Guo-Liang ;

Walton, Michaela ;

Denny, William A. ;

Webb, Victoria L. ;

Copp, Brent R. ;

Harper, Jacquie L. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (21) :9432-9442

[9] Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].

Dömling, A .

CHEMICAL REVIEWS, 2006, 106 (01) :17-89

[10] Synthesis and antimicrobial activity of some new benzimidazole derivatives [J].

El-masry, AH ;

Fahmy, HH ;

Abdelwahed, SHA .

MOLECULES, 2000, 5 (12) :1429-1438

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