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Issue 21, 2014
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Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazine derivatives via multicomponent approach

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Abstract

A series of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazine derivatives 6 were exclusively obtained in high yields for the first time through multicomponent reactions (MCRs) of 2-naphthol, aromatic aldehydes and electron rich primary amines in ethanol at room temperature using CCl3COOH as catalyst. The same reaction could be conducted effectively in solvent-free medium at 100 °C. The stereochemistry of the two hydrogens connected to C-2 and C-4 (1,3) positions of the oxazine ring are identified as anti-orientation by single crystal XRD, COSY and NOESY analysis.

Graphical abstract: Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazine derivatives via multicomponent approach

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Publication details

The article was received on 02 Dec 2013, accepted on 05 Feb 2014 and first published on 06 Feb 2014


Article type: Paper
DOI: 10.1039/C3RA47211F
Citation: RSC Adv., 2014,4, 10912-10917

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    Synthesis of anti-2,3-dihydro-1,2,3-trisubstituted-1H-naphth [1,2-e][1,3]oxazine derivatives via multicomponent approach

    R. Borah, A. K. Dutta, P. Sarma, C. Dutta and B. Sarma, RSC Adv., 2014, 4, 10912
    DOI: 10.1039/C3RA47211F

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