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Current Organic Synthesis

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ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

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Research Article

Novel Synthesis of 4-Benzylidene-2-((1-phenyl-3,4-dihydroisoquinoline-2(1H)-yl)methyl) oxazol-5(4H)-one Derivatives Using 1,2,3,Tetrahydroisoquinoline and their Antimicrobial Activity

Author(s): Nalla Krishna Rao, Tentu Nageswara Rao, Botsa Parvatamma, Y. Prashanthi and Ravi Kumar Cheedarala*

Volume 17, Issue 5, 2020

Page: [396 - 403] Pages: 8

DOI: 10.2174/1570179417666200415151228

Price: $65

Abstract

Aims: A series of six 4-benzylidene-2-((1-phenyl-3,4-dihydro isoquinoline-2(1H)-yl)methyloxazol- 5(4H)-one derivatives were synthesized by condensation of substituted aryl aldehydes with 2-(2-(1-phenyl-3,4- dihydro isoquinoline-2(1H)-acetamido)acetic acid in the presence of sodium acetate, acetic anhydride and zinc oxide as catalysts.

Background: Novel Synthesis of 4-Benzylidene-2-((1-phenyl-3,4-dihy droisoquinoline-2(1H)-yl)methyl)oxazol- 5(4H)-one derivatives using 1,2,3,Tetrahydroisoquinoline and their antimicrobial activity.

Objective: The title compounds can be synthesized from 1,2,3,4-tetrahydroisoquinoline.

Methods: The target molecules, i.e., 4-benzylidene-2-((1-phenyl-3, 4-dihydro isoquinoline-2(1H)-yl) methyl) oxazol-5(4H)-one derivatives (8a-8f) have been synthesized from 1,2,3,4-tetrahydroisoquinoline which was prepared from benzoic acid in few steps.

Results: All the six compounds were evaluated based on advanced spectral data (1H NMR, 13C NMR & LCMS), and the chemical structures of all compounds were determined by elemental analysis.

Conclusion: Antibacterial activity of the derivatives was examined for the synthesized compounds and results indicate that compound with bromine substitution has a good activity profile.

Keywords: Condensation, oxazolone, isoquinoline, antibacterial activity, NMR, antimicrobial activity.

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