Simple aromatic amines from justicia gendarussa. 13C NMR spectra of the bases and their analogues

Tetrahedron
1982.0

Abstract

Four simple o-disubstituted aromatic amines have been isolated from the leaves of Justicia gendarussa Burm and characterized as 2-amino benzyl alcohol (3), 2-(2'-amino-benzylamino) benzyl alcohol (4) and their respective 0-methyl ethers 1 and 2 from 'H NMR and mass spectral analyses of the bases and their acetates. Structures 3 and 4 have also been confirmed by synthesis. Intramolecular hydrogen bonding (cf. 9, 13 and 14) has been envisaged to explain the unexpected shielding of -CH:-OH carbon signals of 3 and 4 on acetylation and upfield displacement of -CH2-N signal of 2a vs 4a in their '3C NMR spectra in CDCI3 solution. ~Jc8 values have been found to be useful for the assignment of aromatic methine carbon signals in o-disubstituted compounds.

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