Tetrahedron p. 6435 - 6440 (1988)
Update date:2022-07-29
Topics:
Ballini, Roberto
Bartoli, Giuseppe
Bosco, Marcella
Dalpozzo, Renato
Marcantoni, Enrico
Conjugate addition of various Grignard reagents to 1-alkyl-2-nitropyrroles and to 2-nitrothiophene has been investigated. 1-Alkyl-2-nitropyrroles undergo alkylation at 3 and 5 positions with prevalence of the latter isomer.On the contrary, in the 2-nitrothiophene system, formation of the 3-isomer prevails.In both systems, a bulkier Grignard reagent favours the 5-isomer formation.This trend can be reversed increasing steric hindrance exerted by the 1-substituent of 2-nitropyrrole. 1-(Tri-isopropylsilyl)-3-nitropyrrole and 3-nitrothiophene give exclusively the 2-isomer.This reaction allows 2-alkyl-3-nitrothiophenes and pyrroles to be synthesized with a one-pot procedure instead of the classical multi stage reaction.
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