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Lewis acid catalyzed Povarov reaction of pentafulvenes and spiro[2,4]-hepta-[4,6]-diene: An efficient access to cyclopentene fused quinolines

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Version 2 2018-03-19, 18:11
Version 1 2018-03-06, 15:25
journal contribution
posted on 2018-03-19, 18:11 authored by Shreyass Saranya, Thekke Veettil Baiju, Greeshma Gopalan, Kokkuvayil Vasu Radhakrishnan

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.

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.

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