Reactions of ortho-lithiophenyl (-hetaryl) isocyanides with carbonyl compounds: rearrangements of 2-metalated 4H-3,1-benzoxazines.
作者： Alexander V. Lygin , Armin de Meijere
DOI: 10.1021/JO9004734
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摘要: ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36−89%, nine examples), 4H-3,1-benzoxazines 9 (45−78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52−75%, four or indolin-2-ones 19 (42−79%, depending on the reaction conditions substitution patterns. Isocyanoalcohols 8, in turn, were converted to under Cu(I) catalysis (66−86%, eight examples). 4H-3,1-Benzoxazin-4-ones 39-Nu isatoic anhydride 40 obtained by 2 carbon dioxide followed trapping lithiated intermediate iodine subsequent reactions nucleophiles (45−60%, three
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