Regioselective preparation of N-substituted 3,5-diamino-1,2,4-oxadiazoles

被引：7

作者：

Suyama, T ^{[1
]}

Suzuki, N ^{[1
]}

Nishimura, M ^{[1
]}

Saitoh, Y ^{[1
]}

Ohkoshi, H ^{[1
]}

Yamaguchi, JI ^{[1
]}

机构：

[1] Kanagawa Inst Technol, Fac Engn, Dept Appl Chem, Atsugi, Kanagawa 2430292, Japan

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 2005年 / 78卷 / 05期

关键词：

Compendex;

D O I：

10.1246/bcsj.78.873

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Regioselective preparation of 3,5-diamino-1,2,4-oxadiazoles which have a substituent on one or the other amino croup has been developed. When]-substituted 3-cyano-2-ethylisourea (2) was allowed to react with hydroxylamine under basic conditions, 5 -amino-3-(substituted amino)-1,2,4-oxadiazole (3) was obtained in good yield. On the other hand. 3-amino-5-(substituted amino)-1,2,4-oxadiazoles (4), a regioisomer of 3, could be synthesized by the reaction of N,O-bis(trimethylsilyl)hydroxylamine (9) with 2 or 1-substituted 3-cyano-2-methylisothiourea (1) and subsequent alcoholysis.

引用

页码：873 / 876

页数：4

共 9 条

[1] 1,2,4-OXADIAZOLES
CLAPP, LB
[J]. ADVANCES IN HETEROCYCLIC CHEMISTRY, 1976, 20 : 65 - 116
[2] The representation of aromatic subsituted guanidine from cyanamide
Kampf, A
[J]. BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1904, 37 : 1681 - 1684
[3] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 1,2,4-OXADIAZOLE DERIVATIVES - HIGHLY POTENT AND EFFICACIOUS AGONISTS FOR CORTICAL MUSCARINIC RECEPTORS
STREET, LJ
BAKER, R
BOOK, T
KNEEN, CO
MACLEOD, AM
MERCHANT, KJ
SHOWELL, GA
SAUNDERS, J
HERBERT, RH
FREEDMAN, SB
HARLEY, EA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (10) : 2690 - 2697
[4] THE ADDITION-REACTION OF N-SILYLAMINES TO N-CYANOAMINO COMPOUNDS
SUYAMA, T
OKUNO, S
KARIYA, M
ICHIKAWA, E
[J]. NIPPON KAGAKU KAISHI, 1987, (01) : 51 - 55
[5] THE REACTION OF N-CYANOCARBONIMIDATE AND RELATED-COMPOUNDS WITH HYDROXYLAMINE
SUYAMA, T
OZAWA, N
SUZUKI, N
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1994, 67 (01) : 307 - 308
[6] SUYAMA T, 1971, YUKI GOSEI KAGAKU KY, V29, P65
[7] SUYAMA T, 1976, YUKI GOSEI KAGAKU KY, V34, P427
[8] THE SYNTHESIS OF 3,5-DIAMINO-1,2,4-OXADIAZOLES .1.
TILLEY, JW
RAMUZ, H
[J]. HELVETICA CHIMICA ACTA, 1980, 63 (04) : 832 - 840
[9] NEW ANIONIC REARRANGEMENTS .15. 1,2-ANIONIC REARRANGEMENT OF ORGANOSILYLHYDROXYLAMINES
WEST, R
BOUDJOUK, P
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (12) : 3987 - 3994

← 1 →