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Synfacts 2011(4): 0373-0373  
DOI: 10.1055/s-0030-1259751
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Extending the Scope of the Biginelli Reaction Using Palladium Catalysis

Contributor(s): Victor Snieckus, Matthew O. Kitching
P. M. Kumar, K. S. Kumar, S. R. Poreddy, P. K. Mohakhud, K. Mukkanti, M. Pal*
Dr. Reddy’s Laboratories Limited, Hyderabad, Jawaharal Nehru Techno-logical University, Hyderabad and University of Hyderabad Campus, India
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

Reported is the application of ortho-iodo benzaldehyde (1) in a three-component Biginelli reaction. By introducing alkyne 4 and a palladium catalyst to the reaction mixture after the formation of the dihydropyrimidinone product, the Sonogashira coupling is effected to give 5 in a one-pot process. Both electron-rich and -poor ­aldehydes (not shown) proved efficacious, and the substitution of the alkyne was well tolerated. Furthermore, this strategy was combined with the Heck and the Suzuki reactions to form further functionalized dihydropyrimidine products 8 and 7.