Multicomponent reactions of urea and its derivatives with CH2O and H2S in the synthesis of 1,3,5-thiadiazinane-4-(thi)ones and macroheterocycles

被引：9

作者：

Akhmetov, Vnira R. ^{[1
]}

Khairullina, Regina R. ^{[1
]}

Bushmarinov, Ivan S. ^{[2
]}

Tyumkina, Tat'yana V. ^{[1
]}

Yanybin, Vasiliy M. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Petrochem & Catalysis, 141 Prospekt Oktyabrya, Ufa 450075, Russia

[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow 119991, Russia

来源：

ARKIVOC | 2011年

关键词：

Urea; guanidine; multicomponent reactions; 1,3,5-thiadiazinane; macroheterocycles; formaldehyde; hydrogen sulfide; X-ray diffraction powder analysis; CYCLOTHIOMETHYLATION; FORMALDEHYDE;

D O I：

10.3998/ark.5550190.0012.811

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient, efficient, and practical method for the synthesis of 1,3,5-thiadiazinan-4-(thi)ones via a multicomponent condensation of urea (or thiourea), formaldehyde and hydrogen sulfide in the presence of a four-fold molar excess of n-BuONa is described. It provides the novel acid-(H2SO4) and base-(n-BuONa)-promoted approach for the one-pot synthesis of the amidine containing macroheterocycles from guanidine and diphenylguanidine. X-ray powder diffraction analysis gave insight into the structure of the 4-methyl-sulfonyl-2H-1,3,5-thiadiazine hydriodide.

引用

页码：149 / 162

页数：14

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