Stereoselective annelation of 3-substituted imidazo[4,5-b]pyridines with cyanoacetylenic alcohols and domino rearrangement of the adducts

Трофимов, Б. А.; Andriyankova, L. V.; Никитина, Л. П.; Belyaeva, Kseniya V.; Малькина, А. Г.; D’yachenko, O. A.; Kazheva, Olga N.; Chekhlov, A. N.; Afonin, A. V.

doi:10.3998/ark.5550190.0013.622

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Cited by 7 publications

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Syntheses and Applications of 2‐Alkynylnitriles

2019

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2-Alkynylnitriles are a distinguished class of molecules known to play a pivotal role in the construction of a plethora of carbo-/heterocyclic compounds of biological and pharmaceutical importance. These molecules have been exploited as hydrolytically stable irreversible labels for cysteine tagging. In addition, they also form an important homologous series of complex interstellar molecules identi-fied by radioastronomy. Therefore, in this Minireview, we highlight the numerous transformations and diverse reactions carried out with these substrates. Different reactions including nucleophilic additions and various carbo-/heterocycles formation are the prime focal areas of this article. Mechanistic aspects for certain reactions have also been delineated. Scheme 1. Synthesis of 3-phenyl-2-propynylnitrile (3) using cyanogen bromide as cyanating agent.Scheme 2. Synthesis of various 2-alkynylnitrile derivatives employing phenyl cyanate (4) as cyanating agent.

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