NOVEL SYNTHESIS OF 5-(ARYLIMINO)-4-(DIALKYLAMINO)-5H-1,2,3-DITHIAZOLES AND THE MECHANISM OF THEIR FORMATION

被引：28

作者：

LEE, H ^{[1
]}

KIM, K ^{[1
]}

WHANG, D ^{[1
]}

KIM, K ^{[1
]}

机构：

[1] POHANG INST SCI & TECHNOL,CTR BIOFUNCT MOLEC,DEPT CHEM,POHANG 790600,SOUTH KOREA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 5-(arylimino)-4-chloro-5H-1,2,3-dithiazo 1 with excess (6 equiv) bulky dialkylamines such as diethyl-, di-n-propyl-, and di-n-butylamines in CH2Cl2 at room temperature gave 5-(arylimino)-4-(dialkylamino)-5H-1,2,3-dithiazoles 5 in 18-76% yields. Compounds 5 are formed via (arylimino)cyanomethyl alkylamino disulfides 3. Nucleophilic addition of the amines to the carbon atom of the cyano group of 3 and subsequent cyclization afford 5.

引用

页码：6179 / 6183

页数：5

共 7 条

[1] SYNTHESIS AND REACTIONS OF 4,5-DICHLORO-1,2,3-DITHIAZOLIUM CHLORIDE
APPEL, R
JANSSEN, H
SIRAY, M
KNOCH, F
[J]. CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (04): : 1632 - 1643
[2] GENERATION OF ESTERS FROM CARBOXYLIC-ACIDS USING APPEL SALT (4,5-DICHLORO-1,2,3-DITHIAZOLIUM CHLORIDE)
FOLMER, JJ
WEINREB, SM
[J]. TETRAHEDRON LETTERS, 1993, 34 (17) : 2737 - 2740
[3] REACTIONS OF 5-(ARYLIMINO)-4-CHLORO-5H-1,2,3-DITHIAZOLES WITH PRIMARY AND SECONDARY ALKYLAMINES - NOVEL SYNTHESIS OF (ARYLIMINO)CYANOMETHYL ALKYLAMINO DISULFIDES AND THEIR MECHANISMS OF FORMATION
LEE, H
KIM, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) : 7001 - 7008
[4] Mayer R., 1984, DD Pat., Patent No. [DD212387, 212387]
[5] Moore JE, 1977, US Pat., Patent No. 4059590
[6] A FACILE SYNTHESIS OF N'-(PARA-TOLUENESULFONYL)-N-ALKYLCYANOFORMAMIDINES, N'-(PARA-TOLUENESULFONYL)-N,N-DIALKYLCYANOFORMAMIDINES AND 1,3-DIALKYL-2-(PARA-TOLUENESULFONYL)GUANIDINES
OH, KC
LEE, H
KIM, KT
[J]. TETRAHEDRON LETTERS, 1992, 33 (34) : 4963 - 4966
[7] POLYSULFUR-NITROGEN HETEROCYCLIC CHEMISTRY
REES, CW
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (03) : 639 - 651

← 1 →