Ultrasound-Assisted, Convenient and Widely Applicable 1,1'-Carbonyl-diimidazole-Mediated "One-Pot" Synthesis of Acyl/Sulfonyl Hydrazines

Author(s): Khalid Mohammed Khan, Uzma Salar, Muhammad Imran Fakhri, Muhammad Taha, Abdul Hameed, Shahnaz Perveen, Wolfgang Voelterd.

Journal Name: Letters in Organic Chemistry

Volume 12 , Issue 9 , 2015

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Abstract:

Acyl / sulfonyl hydrazines were synthesized in a one-pot reaction from carboxylic acid/aryl sulfonic acid in the presence of 1,1-carbonyl diimidazole (CDI) under ultrasound as well as under conventional heating. The reaction was performed on diverse organic molecules including simple benzoic acid (1), electron- donating and electron-withdrawing substituted benzoic acids, biologically active compounds like coumarin-3- carboxylic acid (12), 7-hydroxycoumarin-4-acetic acid (13), and therapeutic drugs like ibuprofen (14), flurbiprofen (15), naproxen (16) or tricyclic adamantane carboxylic acid (17). Benzene sulfonic acid (18) and its derivatives (19, 20, 21 and 22) were used to prepare corresponding sulfonyl hydrazide. All products were synthesized in very good yield via ultrasonic irradiation method and characterized by spectroscopic techniques including EIMS, 1H NMR, 13C NMR, IR. The method was found very simple, facile, efficient and high yielding (>90).

Keywords: Acyl hydrazines, CDI, Ultrasound-assisted, Sulfonyl hydrazines.

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Article Details

VOLUME: 12
ISSUE: 9
Year: 2015
Page: [637 - 644]
Pages: 8
DOI: 10.2174/1570178612666150622184042
Price: $58

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