Hypervalent iodine mediated intramolecular cyclization of thioformanilides: Expeditious approach to 2-substituted benzothiazoles

被引：137

作者：

Bose, D. Subhas ^{[1
]}

Idrees, Mohd. ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Div Organ Chem 3, Fine Chem Lab, Hyderabad 500007, Andhra Pradesh, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 21期

关键词：

D O I：

10.1021/jo0609374

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new, mild, and efficient method has been developed for the synthesis of 2-substituted benzothiazoles via the intramolecular cyclization of thioformanilides by using hypervalent iodine reagents in CH2Cl2 at ambient temperature. The reaction proceeds via a thiyl radical in high yields to give the novel compound oxybis benzothiazole and is also amenable to generating combinatorial libraries of heterocyclic compounds by solid-phase synthesis.

引用

页码：8261 / 8263

页数：3

共 38 条

[1] Hypervalent iodine in the synthesis of bridgehead heterocycles: A facile route to the synthesis of 6-arylimidazo[2,1-b]thiazoles using [hydroxy(tosyloxy)iodo]benzene [J].

Aggarwal, R ;

Sumran, G .

SYNTHETIC COMMUNICATIONS, 2006, 36 (07) :875-879

[2] SYNTHESIS OF 2-SUBSTITUTED BENZOTHIAZOLES FROM 2-FLUOROPHENYLISOTHIOCYANATE [J].

ARES, JJ .

SYNTHETIC COMMUNICATIONS, 1991, 21 (05) :625-633

[3] Novel synthesis of 2-arylbenzothiazoles - Microwave-activated electron transfer [J].

BenAlloum, A ;

Bakkas, S ;

Soufiaoui, M .

TETRAHEDRON LETTERS, 1997, 38 (36) :6395-6396

[4]

Bose DS, 2006, HETEROCYCLES, V68, P1217

[5] An efficient, highly enantioenriched route to L-carnitine and α-lipoic acid via hydrolytic kinetic resolution [J].

Bose, D. Sublias ;

Fatima, Liyakat ;

Rajender, Salla .

SYNTHESIS-STUTTGART, 2006, 11 (11) :1863-1867

[6] An efficient, high yielding protocol for the synthesis of functionalized quinolines via the tandem addition/annulation reaction of o-aminoaryl ketones with α-methylene ketones [J].

Bose, DS ;

Kumar, RK .

TETRAHEDRON LETTERS, 2006, 47 (05) :813-816

[7] Iodine(V) reagents in organic synthesis. Dess-Martin periodinane mediated efficient one-pot oxidation of aldehydes to acyl azides [J].

Bose, DS ;

Reddy, AVN .

TETRAHEDRON LETTERS, 2003, 44 (17) :3543-3545

[8] Reagents for organic synthesis: Use of organostannyl oxides as catalytic neutral agents in the preparation of nitriles from primary amides under microwave irradiation [J].

Bose, DS ;

Jayalakshmi, B .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (05) :1713-1714

[9]

Bose DS, 2002, TETRAHEDRON LETT, V43, P9195

[10] OXIDATION DURING REDUCTIVE CYCLIZATIONS USING BU3SNH [J].

BOWMAN, WR ;

HEANEY, H ;

JORDAN, BM .

TETRAHEDRON, 1991, 47 (48) :10119-10128

← 1 2 3 4 →