A Convenient Method for the Preparation of Benzopyrano- and Furopyrano-2-isoxazoline Derivatives Using Hypervalent Iodine Reagents

Biswanath Das; Harish Holla; Gurram Mahender; Katta Venkateswarlu; B. P. Bandgar

doi:10.1055/s-2005-865314

SHORTPAPER

A Convenient Method for the Preparation of Benzopyrano- and Furopyrano-2-isoxazoline Derivatives Using Hypervalent Iodine Reagents [1]

Biswanath Das*^a, Harish Holla^a, Gurram Mahender^a, Katta Venkateswarlu^a, B. P. Bandgar^b
^a Organic Chemistry Division - I, Indian Institute of Chemical Technology, Hyderabad - 500 007, India, Fax: +91(40)7160512; e-Mail: biswanathdas@yahoo.com;
^b Organic Chemistry Research Laboratory, School of Chemical Sciences, Swami Ramanand Teerth Marathwada University, Vishnupuri, Nanded - 431606, India

Abstract

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Abstract

Treatment of 2-allyloxybenzaldoximes with diacetoxyiodobenzene (DIB) in CH₂Cl₂ at 0 °C to room temperature for 1 hour afforded 3a,4-dihydro-3H-chromeno[4,3-c] isoxazoles in high yields. The method has been extended to the preparation of furopyrano-2-isoxazoline derivatives from 3-O-allyl-1,2-isopropylidene-furanose-5-aldoxaimes derived from d-glucose.

Keywords

aldoxime - sugar - DIB - isoxazoline

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References

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