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

[1] Solid-phase organic reactions III: A review of the literature Nov 96 Dec 97
Booth, S
Hermkens, PHH
Ottenheijm, HCJ
Rees, DC
[J]. TETRAHEDRON, 1998, 54 (51) : 15385 - 15443
[2] Solid-phase synthesis of 1,3-dialkyl quinazoline-2,4-diones
Buckman, BO
Mohan, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4439 - 4442
[3] A GENERAL AND EXPEDIENT METHOD FOR THE SOLID-PHASE SYNTHESIS OF 1,4-BENZODIAZEPINE DERIVATIVES
BUNIN, BA
ELLMAN, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) : 10997 - 10998
[4] 2H-1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES .2. A CONDENSATION OF 2-AMINOBENZENESULFONAMIDE WITH CHLOROALKYL ISOTHIOCYANATES
CHERN, JW
WU, YH
LIU, KC
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) : 1485 - 1488
[5] CHINOIN GYOGYSZER VE, 1997, Patent No. 9707116
[6] Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization cleavage step
Dressman, BA
Spangle, LA
Kaldor, SW
[J]. TETRAHEDRON LETTERS, 1996, 37 (07) : 937 - 940
[7] FUJISAWA PHARM CO, 1988, Patent No. 268990
[8] A general and efficient solid phase synthesis of quinazoline-2,4-diones
Gordeev, MF
Hui, HC
Gordon, EM
Patel, DV
[J]. TETRAHEDRON LETTERS, 1997, 38 (10) : 1729 - 1732
[9] Combinatorial chemistry of natural products: Solid phase synthesis of D- and L-cycloserine derivatives
Gordeev, MF
Luehr, GW
Hui, HC
Gordon, EM
Patel, DV
[J]. TETRAHEDRON, 1998, 54 (52) : 15879 - 15890
[10] Solid phase synthesis of chiral 3-substituted quinazoline-2,4-diones
Gouilleux, L
Fehrentz, JA
Winternitz, F
Martinez, J
[J]. TETRAHEDRON LETTERS, 1996, 37 (39) : 7031 - 7034

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