Accessing Dihydro-1,2-oxazine via Cloke-Wilson-Type Annulation of Cyclopropyl Carbonyls: Application toward the Diastereoselective Synthesis of Pyrrolo[1,2-b][1,2]oxazine

被引:24
作者
Kumar, Pankaj [1 ]
Kumar, Rakesh [1 ]
Banerjee, Prabal [1 ]
机构
[1] Indian Inst Technol Ropar, Dept Chem, Rupnagar 140001, Punjab, India
关键词
DONOR-ACCEPTOR CYCLOPROPANES; 3+2 CYCLOADDITION; RING; PYRROLIDINE; DERIVATIVES; OXIMES; REARRANGEMENT; ISOXAZOLINE; NITRONES; RULES;
D O I
10.1021/acs.joc.0c00531
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it shows negligible sensitivity toward air/moisture. Dihydro-4H-1,2-oxazines when subjected to cycloaddition with the cyclopropane diester afford a trouble-free formulation of the valued hexahydro-2H-pyrrolo[1,2-b][1,2]oxazine derivatives. A cascade one-pot variant of this two-step strategy offers a comparable overall yield of the final product.
引用
收藏
页码:6535 / 6550
页数:16
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