Expeditious synthesis of cyclic isourea derivatives of β-D-glucopyranosylamine

被引：13

作者：

López, O ^{[1
]}

Maya, I ^{[1
]}

Ulgar, V ^{[1
]}

Robina, I ^{[1
]}

Fernández-Bolaños, JG ^{[1
]}

机构：

[1] Univ Seville, Fac Quim, Dept Quim Organ, E-41071 Seville, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 24期

关键词：

thiourea desulfurization; cyclizations; mercury(II) oxide; isoureas; ureas; trehazolin;

D O I：

10.1016/S0040-4039(02)00798-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Alkylamino. dialkylamino. arylamino)tetrahydropyrano[2.3-d]oxazoles are prepared in good yield by a one-pot three-step synthesis from O-unprotected beta-D-glucopyranosylamine, by its transformation into glucopyranosyl isothiocyanate in dioxane-water. coupling with amines, and reaction of the corresponding thioureas with yellow mercury (II) oxide in the same reaction medium. In the case of diethylamine prolonged reaction time during the last step, with an extra portion of yellow HgO led to N.N-diethyl-N'-(beta-D-glucopyranosyl)urea in a one-pot four-step synthesis. 2-(beta-D-Glucopyranosylamino)tetrahydro-pyrano[2,3-d]oxazole. an analogue of trehazolin. is obtained in good yield by cyclocondensation of 1.3-bis(beta-D-glucopyranosyl)thiourea. (C), 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：4313 / 4316

页数：4

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