SYNTHESIS OF 2-HYDROXYMETHYLENE- AND 2-DIMETHYLAMINOMETHYLENE-3-OXOQUINUCLIDINES AND THEIR REACTIONS WITH NUCLEOPHILIC REAGENTS

Article abstract of DOI:10.1007/BF00513439

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 pyrazolo<3,4-b>- and pyrimido<5,4-b>quinuclidines with aryl or heteroaryl substituents in the resulting ring, was studied.