Tetrahedron letters

Expedient synthesis of 1-vinylpyrrole-2-carbaldehydes

…, AV Ivanov, EY Schmidt, AM Vasil'tsov, BA Trofimov

Index: Mikhaleva, Al'bina I.; Zaitsev, Alexey B.; Ivanov, Andrey V.; Schmidt, Elena Yu.; Vasil'tsov, Alexander M.; Trofimov, Boris A. Tetrahedron Letters, 2006 , vol. 47, # 22 p. 3693 - 3696

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Citation Number: 33

Abstract

1-Vinylpyrrole-2-carbaldehydes and 1-vinyl-4, 5-dihydrobenzo [g] indole-2-carbaldehyde were synthesized in 56–91% yields from their 1-vinyl derivatives by a modified Vilsmeier– Haack reaction. A low temperature (− 78° C) is required to avoid removal of the N-vinyl group, whereas at elevated temperature (reflux in 1, 2-dichloroethane) the latter process leads to direct conversion of 1-vinylpyrroles to pyrrole-2-carbaldehydes.