Synthesis of heterocycles & carbocycles using baylis-hillman adducts and synthesis of indene-spiro-oxindoles using tandem prins and friedel-crafts reactions

Abstract

The Baylis-Hillman reaction is a three component atom economy carbon-carbon bond forming reaction. It involves the coupling of and#945;-position of an activated alkene with an electrophile under the influence of a catalyst or catalytic system providing interesting classes of densely functionalized molecules, which have been used in various organic synthetic transformation methodologies and also in synthesis of various natural products and bio-active molecules. Our research group has been working on this fascinating reaction for the last several years with a view to expand the scope of the applications of Baylis-Hillman adducts in organic synthesis. This thesis deals with the synthesis of heterocycles and carbocycles using the Baylis-Hillman adducts and synthesis of indene-spiro-oxindoles using the Prins-Friedel-Crafts reactions and consists of three chapters 1) Introduction 2) Objectives, Results and Discussion and 3) Experimental. The first chapter i.e., Introduction presents a brief literature survey on the developments of Baylis-Hillman reaction and also on the application of the Baylis-Hillman adducts in the synthetic organic chemistry. The second chapter deals with the objectives, results and discussion. With a view to study the application of Baylis-Hillman adducts for the synthesis of heterocyclic and carbocyclic molecules and with a view to develop a simple synthesis of spiro oxindole via the tandem. Prins and Friedel-Crafts reactions we have undertaken a research program with following objectives. newline1) To develop a simple and one-pot synthesis of benzo[b][1,8]naphthyridones from the Baylis-Hillman adducts. 2) To develop a simple facile and multi-step one-pot synthesis of quinoline derivatives from the Baylis-Hillman acetates. 3) To develop a simple synthesis of bicyclic frameworks containing benzocyclohe-ptane moiety and tetracyclic carbocyclic framework containing 6,7,6,6 ring systems from the Baylis-Hillman acetates.