A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero–Diels–Alder reaction

Shinde, V and A, Sagar and D S, Sharada (2015) A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero–Diels–Alder reaction. Organic and Biomolecular Chemistry, 13. pp. 7614-7618. ISSN 1477-0520

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Abstract

We have demonstrated for the first time the use of 2H-indazole as a diene partner in an aza hetero–Diels–Alder reaction leading to highly substituted 4-aminoquinolines via a heterocylic–heterocylic (H–H) strategy and have further developed a tandem one-pot method starting from 2-azidobenzaldehyde by the formation of 2C–N, 1N–N and 1C–C bonds. The key features of the present protocol are readily available starting materials, mild reaction conditions, being work-up free and having easy purification. This is the first time where the synthesis of 4-aminoquinoline drug like molecules has been achieved starting from simple starting materials in an atom economical manner.

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IITH Creators:
IITH CreatorsORCiD
D S, SharadaUNSPECIFIED
Item Type: Article
Subjects: ?? sub5.8 ??
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 30 Jul 2015 11:50
Last Modified: 22 Feb 2016 05:59
URI: http://raiithold.iith.ac.in/id/eprint/1727
Publisher URL: http://dx.doi.org/10.1039/C5OB01023C
OA policy: http://www.sherpa.ac.uk/romeo/issn/1477-0520/
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