Solid-phase synthesis of 2-substituted-3-(substituted sulfanyl)-1,2,4-benzothiadiazine 1,1-dioxide library

被引：15

作者：

Makino, S ^{[1
]}

Okuzumi, T ^{[1
]}

Nakanishi, E ^{[1
]}

Tsuji, T ^{[1
]}

机构：

[1] Ajinomoto Co Inc, Pharmaceut Res Labs, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(02)01862-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first solid-phase synthesis of 2-substituted-3-(substituted sulfanyl)-1,2,4-benzothiadiazine 1,1-dioxides has been developed. Synthesis of the title compounds was achieved as follows: (1) sulfonylation of solid-supported primary amines with 2-nitrobenzenesulfonylchlorides, (2) reduction of the nitro group, (3) cyclization with thiocarbonyldiimidazole (formation of thiourea), (4) S-alkylation or S-arylation of the thiourea. In addition to the excellent purity of the product, a large-size library can be synthesized with the method as this synthesis includes three diversity points. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：8401 / 8403

页数：3

共 23 条

[21] Synthesis and applications of small molecule libraries [J].

Thompson, LA ;

Ellman, JA .

CHEMICAL REVIEWS, 1996, 96 (01) :555-600

[22] Solid phase synthesis of Fmoc N-methyl amino acids: Application of the Fukuyama amine synthesis [J].

Yang, LH ;

Chiu, KL .

TETRAHEDRON LETTERS, 1997, 38 (42) :7307-7310

[23] Solid-phase synthesis of substituted 4-acyl-1,2,3,4-tetrahydroquinoxalin-2-ones [J].

Zaragoza, F ;

Stephensen, H .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (07) :2555-2557

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