Abstract
Imines of 1-methyl-3-amino-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepine-2-one undergo thermal (toluene, 110°C) or LiBr-DBU catalysed (MeCN, room temperature) regio- and stereo-specific cycloaddition to a range of achiral and chiral dipolarophiles giving racemic and homochiral spiro (pyrrolidinyl-2,3′-benzodiazepine) cycloadducts respectively in excellent yield. The reactions proceed via intermediate NH azomethine ylides and litho azomethine ylides respectively. Imines of 1-methyl-3-imino-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepine-2-one undergo thermal (toluene, 110°C) or LiBr-DBU catalysed (MeCN, room temperature) regio- and stereo-specific cycloaddition to a range of achiral and chiral dipolarophiles giving racemic and homochiral spiro (pyrrolidinyl-2,3′-benzodiazepine) cycloadducts respectively in excellent yield.
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