3-Pyrrolidino-2-benzopyran-1-one behaves differently towards various 1,3-dipoles : diphenyl-nitrite imine gives the pyrazolobenzopyranone (3), benzonitrile oxide and N-benzylideneaniline N-oxide yield derivatives (6) and (7), respectively, of 2,3-benzoxazepin-1-one, and p-nitrophenyl azide forms a mixture of 2-p-nitrophenyl-3-(N-pyrrolidinecarbonyl)phthalimidine (10) and N-(p-nitrophenylcarbamoyl)pyrrolidine (13).
G. V. Boyd and R. L. Monteil, J. Chem. Soc., Perkin Trans. 1, 1980, 846 DOI: 10.1039/P19800000846
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