ONE-POT SYNTHESIS OF 4,5-DIHYDRO-3,1-BENZOXAZEPINE-2(1H)-THIONES FROM 2-(2-ISOCYANOPHENYL)ETHANOLS VIA THE CORRESPONDING ISOTHIOCYANATES

被引：5

作者：

Fukamachi, Shuhei ^{[1
]}

Konishi, Hisatoshi ^{[1
]}

Kobayashi, Kazuhiro ^{[1
]}

机构：

[1] Tottori Univ, Grad Sch Engn, Div Appl Chem, Dept Chem & Biotechnol, Tottori 6808552, Japan

来源：

HETEROCYCLES | 2011年 / 83卷 / 04期

基金：

日本学术振兴会;

关键词：

4,5-Dihydro-3,1-benzoxazepine-2(1H)-thione; 2-(2-Isocyanophenyl)ethanol; Isothiocyanate; 2-(Lithiomethyl)phenyl Isocyanide; Sulfur; ISOCYANIDES; DERIVATIVES;

D O I：

10.3987/COM-11-12142

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the preparation of 4,5-dihydro-3,1-benzoxazepine-2(1H)-thiones under mild conditions has been developed. 2-(2-Isocyanophenyl)ethanols, easily accessible by treating 1-isocyano-2-(lithiomethyl)benzenes with aldehydes or ketones, were converted into the corresponding isothiocyanates on treatment with sulfur in the presence of a catalytic amount of selenium and excess triethylamine. These isothiocyanato alcohols were then treated with sodium hydride to give 4,5-dihydro-3,1-benzoxazepine-2(1H)-thione derivatives in one pot.

引用

页码：883 / 889

页数：7

共 7 条

[1] NOVEL SELENIUM CATALYZED SYNTHESIS OF ISOTHIOCYANATES FROM ISOCYANIDES AND ELEMENTAL SULFUR [J].

FUJIWARA, S ;

TSUTOMU, S ;

SONODA, N ;

AOKI, M ;

OKADA, K ;

MIYOSHI, N ;

KAMBE, N .

TETRAHEDRON LETTERS, 1991, 32 (29) :3503-3506

[2]

ITO Y, 1978, TETRAHEDRON LETT, P2087

[3] SYNTHESIS OF N-FORMYLINDOLINE DERIVATIVES BY LEWIS ACID-CATALYZED CYCLIZATIONS OF ORTHO-(2-HYDROXYALKYL)PHENYL ISOCYANIDES [J].

ITO, Y ;

KOBAYASHI, K ;

SAEGUSA, T .

CHEMISTRY LETTERS, 1980, (12) :1563-1566

[4] INDOLE SYNTHESES UTILIZING ORTHO-METHYLPHENYL ISOCYANIDES [J].

ITO, Y ;

KOBAYASHI, K ;

SEKO, N ;

SAEGUSA, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (01) :73-84

[5]

KATAYAMA S, 2006, Patent No. 2006132295

[6]

Rodgers J. D., 2000, PCT Int. Appl., Patent No. [2000000479, WO 2000000479A1]

[7]

RODGERS JD, 2001, Patent No. 20016204262

← 1 →