First Friedel-Crafts
Reaction of the Baylis-Hillman Adducts Derived from Nitroolefins:
Application towards Synthesis of Pyrrolidines and Spiropyrrolidines

Manickam Bakthadoss; Nagappan Sivakumar

doi:10.1055/s-0030-1260557

LETTER

First Friedel-Crafts Reaction of the Baylis-Hillman Adducts Derived from Nitroolefins: Application towards Synthesis of Pyrrolidines and Spiropyrrolidines

Manickam Bakthadoss*, Nagappan Sivakumar
Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
Fax: +91(44)22352494; e-Mail: bhakthadoss@yahoo.com;

Abstract

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Abstract

A general and simple protocol for the arylation of Baylis-Hillman adducts derived from nitroolefins leading to novel classes of (E)-2-nitro-1,3-diarylprop-1-enes and 1-[(E)-2-nitro-3-arylallyl]naphthalenes via an intermolecular Friedel-Crafts reaction have been achieved. Further application of these compounds has been demonstrated for the synthesis of pyrrolidines and 3-spiropyrrolidines which are integral components of many natural products and bioactive molecules.

Key words

Baylis-Hillman reaction - Friedel-Crafts reaction - intermolecular [3+2] cycloaddition - arylation - spiro compounds

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