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
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Kumar, Pankaj
[1
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Kumar, Rakesh
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Banerjee, Prabal
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Indian Inst Technol Ropar, Dept Chem, Rupnagar 140001, Punjab, IndiaIndian Inst Technol Ropar, Dept Chem, Rupnagar 140001, Punjab, India
Banerjee, Prabal
[1
]
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[1] Indian Inst Technol Ropar, Dept Chem, Rupnagar 140001, Punjab, India
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.
机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Wei, Wen
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Tang, Yuhai
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Tang, Yuhai
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Zhou, Yan
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Zhou, Yan
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Deng, Ge
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Deng, Ge
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Liu, Ziyu
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Liu, Ziyu
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Wu, Jun
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Wu, Jun
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Li, Yang
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Li, Yang
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Zhang, Junjie
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Zhang, Junjie
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Xu, Silong
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Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R ChinaXi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Wei, Wen
;
Tang, Yuhai
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Tang, Yuhai
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Zhou, Yan
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Zhou, Yan
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Deng, Ge
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Deng, Ge
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Liu, Ziyu
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Liu, Ziyu
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Wu, Jun
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Wu, Jun
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Li, Yang
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Li, Yang
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Zhang, Junjie
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机构:Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China
Zhang, Junjie
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Xu, Silong
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Xi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R ChinaXi An Jiao Tong Univ, Dept Chem, Sch Sci, Xian 710049, Shaanxi, Peoples R China