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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 7
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Original Articles

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

Shreyass SaranyaOrganic Chemistry Section, Chemical Science and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, IndiaView further author information
,
Thekke Veettil BaijuOrganic Chemistry Section, Chemical Science and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, India;Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST, Thiruvananthapuram, IndiaView further author information
,
Greeshma GopalanOrganic Chemistry Section, Chemical Science and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, India;Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST, Thiruvananthapuram, IndiaView further author information
&
Kokkuvayil Vasu RadhakrishnanOrganic Chemistry Section, Chemical Science and Technology Division, National Institute for Interdisciplinary Science and Technology (CSIR), Thiruvananthapuram, India;Academy of Scientific and Innovative Research (AcSIR), CSIR-NIIST, Thiruvananthapuram, IndiaCorrespondence[email protected]
View further author information
Pages 816-829 | Received 20 Dec 2017, Published online: 06 Mar 2018
 
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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.

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