Synthesis of Tetrahydropyrazolo[4',3':5,6]pyrano[3,4-c]quinolones by Domino Knoevenagel/Hetero Diels

Synthesis of Tetrahydropyrazolo[4',3':5,6]pyrano[3,4-c]quinolones by Domino Knoevenagel/Hetero Diels–Alder Reactions

Published:2019-08-14 Issue:15 Volume:30 Page:1782-1786
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Kiamehr Mostafa¹,Mohammadkhani Leyla¹,Khodabakhshi Mohammad Reza²,Jafari Behzad³,Langer Peter³⁴^ORCID

Affiliation:

1. Department of Chemistry, Faculty of Science, University of Qom

2. Applied Biotechnology Research Center, Baqiyatallah University of Medical Sciences

3. Institut für Chemie, Universität Rostock

4. Leibniz-Institut für Katalyse e.V. an der Universität Rostock

Abstract

An efficient Lewis acid mediated domino Knoevenagel/hetero Diels–Alder (DKHDA) reaction of pyrazolone derivatives with N-acrylated anthranilic aldehydes was developed, which afforded functionalized tetracyclic tetrahydropyrazolo[4',3':5,6]pyrano[3,4-c]quinolones. The products were formed in good yields and with excellent regio- and stereoselectivity in favor of the cis-configured isomer.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0039-1690189.pdf

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