Issue in Honor of Dr. Jhillu S. Yadav
ARKIVOC 2016 (ii) 172-205
Intramolecular Baylis-Hillman reaction: synthesis of heterocyclic molecules Deevi Basavaiah*and Guddeti Chandrashekar Reddy School of Chemistry, University of Hyderabad, Hyderabad, 500 046, India E-mail:
[email protected] ,
[email protected] Dedicated to Dr. J. S. Yadav on his 65th birthday DOI: :http://dx.doi.org/10.3998/ark.5550190.p009.322 Abstract The Baylis-Hillman (BH) [also known as the Morita-Baylis-Hillman (MBH)] reaction is a versatile atom-economic C-C bond forming reaction between the α-position of activated alkenes and electrophiles under the influence of a catalyst and provides interesting classes of densely functionalized molecules. Its intramolecular version is yet another fascinating reaction by itself, producing various carbocylic and heterocyclic compounds of synthetic and medicinal relevance. Applications of the intramolecular Baylis-Hillman reaction in obtaining heterocyclic molecules of different ring sizes and also to the synthesis of various natural products/bioactive compounds containing heterocyclic frameworks are presented in this brief review. Keywords: Baylis-Hillman reaction, Rauhut-Currier reaction, activated alkene, electrophile, heterocyclic molecules, natural products
Table of Contents 1. Introduction: the Baylis-Hillman (BH) Reaction 2. Intramolecular Baylis-Hillman (IBH) Reactions 2.1. IBH reactions: Activated alkene (α,β-unsaturated ester)-aldehyde system 2.2. IBH reactions: Activated alkenes (α,β-unsaturated sulfonates or α,β-unsaturated sulfonamides)-aldehyde system 2.3. IBH reactions: Activated alkene (α,β-unsaturated amide)-aldehyde system 2.4. IBH reactions: Activated alkene (α,β-unsaturated sulfonamide)-ketone system 2.5. IBH reactions: Activated alkene (α,β-unsaturated amide)-ketone system 2.6. IBH reactions: Activated alkene (vinylquinoline)-imine system 2.7. Unusual Intramolecular Baylis-Hillman reactions Page 172
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