Two‐stage Regioselective Access to Non‐symmetric 3, 5‐Diarylisoxazoles: Synthesis of Combretastatin A‐4 analogues. Issue 12 (10th November 2021)

• Record Type: Journal Article
• Authors: Karetnikov, Georgy L.; Skvortsov, Dmitry A.; Lopatukhina, Elena V.; Nikolaeva, Svetlana N.; Bondarenko, Oksana B.
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 12(2021)
• Page Start: 3343
• Page End: 3348
• Publication Date: 2021-11-10
• Subjects: 2-aryl-1, 1-dibromocyclopropanes -- 3-aryl-5-bromoisoxazoles -- CA-4 analogues -- nitrosation/Suzuki arylation sequence -- non-symmetric 3, 5-diarylisoxazoles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100551
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: A new two‐stage regioselective access to non‐symmetric 3, 5‐diarylisoxazoles starting from readily available 2‐aryl‐1, 1‐dibromocyclopropanes is developed. The strategy based on the nitrosation/Suzuki arylation sequence ensures good yields of the products and a wide scope of substituents in both aryl rings. Using this strategy, a panel of combretastatin A‐4 (CA‐4) analogues presented by 3, 5‐diarylisoxazole structural motif was synthesized and evaluated for their biological activity Abstract : A new two ‐stage regioselective access to non‐symmetric 3, 5‐diarylisoxazoles starting from readily available 2‐aryl‐1, 1‐dibromocyclopropanes is developed. The strategy based on the nitrosation/Suzuki arylation sequence ensures good yields of the products and a wide scope of substituents in both aryl rings.