Synthesis of 2-hydroxymethylene- and 2-dimethylaminomethylene-3-oxoquinuclidines and their reactions with nucleophilic reagents

The reaction of 3-oxoquinuclidine with ethyl formate in the presence of sodium and with dimethylformamide diethylacetal was used to synthesize 2-hydroxymethylene- and 2-dimethylaminomethylene-3-oxoquinuclidines, which upon reaction with amines from N-substituted 2-aminomethylene-3-oxoquinuclidines and upon reaction with hydrazine hydrate give pyrazolo 3,4-b]quinuclidines. The reaction of 2-aryl- and 2-heteroarylmethylene-3-oxoquinuclidines with hydrazine hydrate and thiourea, which led to the synthesis of pyrazolo3,4-b]- and pyrimido5,4-b]quinuclidines with aryl or heteroaryl substituents in the resulting ring, was studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1232–1237, September, 1982.