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- Title
PIDA Mediated Synthesis of Benzopyranoisoxazoles via an Intramolecular Nitrile Oxide Cycloaddition (INOC): Application to the Synthesis 4H‐chromeno[4,3‐c]isoxazol‐4‐ones.
- Authors
Maurya, Rohit Kumar; Kumar, Shubham; Kumar, Vikash; Dey, Ashutosh; Patlolla, Ravinder Reddy; Burra, Amarender Goud; Khatravath, Mahender
- Abstract
Presented herein is an approach for the synthesis of highly substituted tricyclic benzopyranoisoxazoles from the corresponding aldoximes via an intramolecular nitrile oxide cycloaddition (INOC) reaction using a hypervalent iodine reagent (Diacetoxyiodo)benzene (PIDA/DIB/(PhI(OAc)2) as the single inexpensive oxidizing agent. The key step involved in this reaction is a sequential intramolecular C−C and C−O bond formation. A variety of benzopyranoisoxazoles were constructed in moderate to high yields. In addition, some of the benzopyranoisoxazoles were converted to 4H‐chromeno[4,3‐c]isoxazol‐4‐ones via allylic oxidation using CrO3 as an oxidant.
- Subjects
NITRILE oxides; RING formation (Chemistry); HYPERVALENCE (Theoretical chemistry); OXIDIZING agents; ALDOXIMES; OXIDATION; BENZENE derivatives
- Publication
Asian Journal of Organic Chemistry, 2023, Vol 12, Issue 11, p1
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.202300410