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A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes
Nikita E Golantsov1, Alexandra S Golubenkova1, Alexey A Festa1
1Organic Chemistry Department, Science Faculty, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow 117198, Russia.
Abstract:
The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-three-component process and forms imidazolidines with an N-vinylpropargylamine fragment. Heating the resulting imidazolidines in xylene on air leads to an effective formation of polysubstituted pyrroles through a domino sequence of aza-Claisen rearrangement/transannular nucleophilic addition/oxidative ring opening reactions. The direct one-pot transformation of 2-imidazolines to pyrroles has been also realized.
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