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

Autor:	Rozentsveig, Igor B., Serykh, Valery Yu., Chernysheva, Gulnur N., Kondrashov, Evgeniy V., Fedotova, Alena I., Ushakov, Igor A., Tretyakov, Evgeny V., Romanenko, Galina V.
Předmět:	CHEMICAL reactions NUCLEOPHILIC addition (Chemistry) ADDITION reactions CHEMICAL derivatives HETEROCYCLIC compounds
Zdroj:	European Journal of Organic Chemistry; 10/15/2014, Vol. 2014 Issue 29, p6547-6557, 11p
Abstrakt:	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-α]pyrimidin-3-ylsulfonamides in the presence of NaOH, whereas the expected isomeric imidazo[1,2-α]-pyrimidin-2-ylsulfonamides are not formed. A tentative mechanism for the formation of annulated heterocyclic derivatives through Dimroth rearrangement has been proposed. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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