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ABSTRACT
An efficient protocol for the Lewis acid catalyzed three-component aza-Diels-Alder reaction of pentafulvenes as dienophile has been developed. Cyclopentene fused tetrahydroquinolines were formed in good yields with excellent diastereoselectivities. The method was extended to spiro[2,4]hepta-4,6-diene, by which 3,4-dihydroquinoline derivatives were obtained. The aromatization of cycloadducts furnished corresponding quinoline derivatives.
GRAPHICAL ABSTRACT
Acknowledgments
BTV and GG thank CSIR for research fellowship. Dr. Sunil Varughese is greatly acknowledged for single X-ray crystal analyses. The authors also thank Mrs. Saumini Mathew, Mr. Saran P.Raveendran, Mrs. S. Viji and Ms. S. Aathira of CSIR-NIIST for recording NMR and Mass spectra.
Additional information
Funding
Financial assistance from the Science and Engineering Research Board (SERB) New Delhi (SB/S1/OC-24/2014) and the Council of Scientific and Industrial Research, New Delhi (12th FYP project, ORIGIN-CSC-0108) are greatly acknowledged.