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Issue 28, 2015
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A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero–Diels–Alder reaction

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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.

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

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Publication details

The article was received on 21 May 2015, accepted on 03 Jun 2015 and first published on 22 Jun 2015


Article type: Communication
DOI: 10.1039/C5OB01023C
Org. Biomol. Chem., 2015,13, 7614-7618

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

    S. Vidyacharan, A. Sagar and D. S. Sharada, Org. Biomol. Chem., 2015, 13, 7614
    DOI: 10.1039/C5OB01023C

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