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Two‐Step Regioselective Synthesis of 3‐(Sulfonylamino)imidazo[1,2‐ a ]pyrimidines from 2‐Aminopyrimidines and N ‐(2,2‐Dichloro‐2‐phenylethylidene)arensulfonamides
Author(s) -
Rozentsveig Igor B.,
Serykh Valery Yu.,
Chernysheva Gulnur N.,
Kondrashov Evgeniy V.,
Fedotova Alena I.,
Ushakov Igor A.,
Tretyakov Evgeny V.,
Romanenko Galina V.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402695
Subject(s) - chemistry , regioselectivity , medicinal chemistry , nucleophile , nucleophilic addition , reaction mechanism , stereochemistry , organic chemistry , catalysis
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.