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Vinylation of Nitro‐Substituted Indoles, Quinolinones, and Anilides with Grignard Reagents
Author(s) -
Egris Riccardo,
Villacampa Mercedes,
Menéndez J. Carlos
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901322
Subject(s) - nitro , chemistry , moiety , substituent , reagent , indole test , grignard reagent , organic chemistry , combinatorial chemistry , alkyl
The reaction of vinyl Grignard reagents with o ‐methoxynitroarenes containing an electron‐releasing substituent para to the nitro group proceeds through a pathway that is different from the initially expected Bartoli indole synthesis. Thus, instead of giving fused indole derivatives, these reactions provide a very mild and efficient new procedure for the synthesis of synthetically relevant aromatic systems containing an o ‐nitrovinyl moiety, such as 5‐nitro‐4‐vinylindoles, 6‐nitro‐7‐vinylindoles, 6‐nitro‐5‐vinyl‐2(1 H )quinolinones, and 4‐nitro‐3‐vinylanilines.