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Report | Regular issue | Vol 22, No. 12, 1984, pp.2815-2820
Published online, 1st January, 1970
DOI: 10.3987/R-1984-12-2815
Novel Heterocycles. 11. Synthesis of the Spiro[pyrrolidine-3,2’(1’H)-quinazoline]ring System

Gary M. Coppola* and Michael J. Shapiro

*Sandoz Research Institute, Sandoz, Inc., Route 10, East Hanover, New Jersey 07936, U.S.A.


The reaction of amines with 1 and 2 was investigated. When 1 or 2 was treated with ammonia only the monoamide 3 was formed. An analogous reaction of 2 with methylamine produced the diamide 4 whereas 1 yielded the spiro imide 6 contaminated with minor amounts of 4. Compound 6 was also obtained from the alkylation of 3 with methyl iodide. The reaction of equimolar amounts of 2 and benzylamine furnished the spiro imide 5. Some spectral data, including carbon-13 assigments, are also discussed.