Two-Step Regioselective Synthesis of 3-(Sulfonylamino)imidazo-[1,2-a]pyrimidines from 2-Aminopyrimidines and N-( 2,2-Dichloro-2-phenylethylidene)arensulfonamides

被引：16

作者：

Rozentsveig, Igor B. ^{[1
]}

Serykh, Valery Yu ^{[1
]}

Chernysheva, Gulnur N. ^{[1
]}

Kondrashov, Evgeniy V. ^{[1
]}

Fedotova, Alena I. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Tretyakov, Evgeny V. ^{[2
]}

Romanenko, Galina V. ^{[2
]}

机构：

[1] Russian Acad Sci, Siberian Branch, AE Favorsky Irkutsk Inst Chem, Irkutsk 664033, Russia

[2] Russian Acad Sci, Siberian Branch, Int Tomog Ctr, Novosibirsk 630090, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 29期

关键词：

Nitrogen heterocycles; Sulfonamides; Nucleophilic addition; Rearrangement; Regioselectivity; MULTICOMPONENT REACTIONS; DERIVATIVES; ALDEHYDES; N-(2,2-DICHLORO-2-PHENYLETHYLIDENE)ARENESULFONAMIDES; ANIONS; ACID;

D O I：

10.1002/ejoc.201402695

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of 2-aminopyrimidines with N-(2,2-dichloro-2-phenylethylidene) arenesulfonamides affords the corresponding products of nucleophilic addition to the azomethine group, N-[2,2-dichloro-2-phenyl-1-(heterylamino)ethyl]sulfonamides, in good yields. The latter are easily cyclized to give imidazo[1,2-a]pyrimidin-3-ylsulfonamides in the presence of NaOH, whereas the expected isomeric imidazo[1,2-a]pyrimidin-2-ylsulfonamides are not formed. A tentative mechanism for the formation of annulated heterocyclic derivatives through Dimroth rearrangement has been proposed.

引用

页码：6547 / 6557

页数：11

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