An efficient entry to 1, 2-benzisoxazoles via 1, 3-dipolar cycloaddition of in situ generated nitrile oxides and benzyne

…, DJ Ritson, P Sharma, S Keeling, JE Moses

文献索引：Spiteri, Christian; Mason, Christopher; Zhang, Fengzhi; Ritson, Dougal J.; Sharma, Pallavi; Keeling, Steve; Moses, John E. Organic and Biomolecular Chemistry, 2010 , vol. 8, # 11 p. 2537 - 2542

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被引用次数: 19

摘要

An alternative strategy involves the simultaneous formation of the 3-3a and 7a-1 bonds, via a Huisgen-type 6 1,3-dipolar cycloaddition of benzyne (3) with nitrile oxides (4) (Scheme 2). 4b,7 Unfortunately, such reactions generally suffer from low yields, mainly due to competing side-reaction pathways resulting from the highly reactive intermediates. ... Scheme 2 Reaction pathways of nitrile oxides 4. ... In general, the reactive nitrile oxide species (4) are first ...