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Synthesis 2005(10): 1572-1574  
DOI: 10.1055/s-2005-865314
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

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

Biswanath Das*a, Harish Hollaa, Gurram Mahendera, Katta Venkateswarlua, B. P. Bandgarb
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
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Publication History

Received 25 January 2005
Publication Date:
18 April 2005 (online)

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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

1

Part 60 in series ‘Studies on Novel Synthetic Methodologies’, IICT Communication No. 050220.

1

Part 60 in series ‘Studies on Novel Synthetic Methodologies’, IICT Communication No. 050220.