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
收藏
页码：6547 / 6557
页数：11
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