N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIV.* Synthesis and Reactivity of the New Benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine Ring System

被引：2

作者：

Innes, Dylan ^{[1
]}

Perkins, Michael V. ^{[1
]}

Liepa, Andris J. ^{[2
]}

Francis, Craig L. ^{[2
]}

机构：

[1] Flinders Univ S Australia, Sch Chem & Phys Sci, Bedford Pk, SA 5042, Australia

[2] CSIRO, Ian Wark Lab, Biomed Synthet Chem Grp, Clayton, Vic 3168, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 2018年 / 71卷 / 01期

关键词：

ALUMINUM-HYDRIDE; AMINE COMPLEXES; DERIVATIVES;

D O I：

10.1071/CH17255

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N,N-Dialkyl-N'-chlorosulfonyl chloroformamidines 1 underwent regioselective reactions with the 1,3-NCCbis-nucleophilic 1H-benzimidazole-2-acetonitriles 4 and related compounds to produce benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine dioxides 6, 9, 12, and 14, representatives of a new ring system. Reaction of dichlorides 1 with trifluoroacetyl derivative 16 afforded benzo[4,5]imidazo[1,2-c]pyrimidines 19 and 20. An N-acyl and some N-alkyl derivatives of benzimidazo-thiadiazines 6 were prepared to demonstrate the potential of this new ring system as a novel scaffold for synthetic and medicinal chemistry applications. Treatment of the 4-cyano-5-methyl-benzimidazo-thiadiazine 26c with LiAlH4 resulted in an unexpected and remarkable conversion of the nitrile to give the 4,5-dimethyl-benzimidazo-thiadiazine 29.

引用

页码：58 / 69

页数：12

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