Journal of the Chemical Society. Perkin transactions I p. 481 - 486 (1980)
Update date:2022-08-02
Topics:
Bajwa, Joginder S.
Sykes, Peter J.
The reaction of 3-aminopyrazole and its 4-cyano-derivative with 2-hydroxymethylene-3-oxo-steroids gave a mixture of angularly fused and linearly fused products, androst-2-eno<2,3-g>- and androstano<3,2-f>-pyrazolo<1,5-a>pyrimidines, respectively.However, the condensation of 3-amino-4-cyano-5-cyanomethylpyrazole with 2-hydroxymethyl-3-oxo-steroids gave only angularly fused products, namely, androst-2-eno<2,3-g>pyrazolo<1,5-a>pyrimidines.The reaction of 3-aminopyrazole and its derivatives with a 2-hydroxymethylene-Δ4-3-oxo-steroid and 16-hydroxymethylene-17-oxo-steroids also afforded only the angularly fused products, androst-2,4-dieno<2,3-g>- and androst-16-eno<16,17-g>-pyrazolo<1,5-a>pyrimidines, respectuvely.The structures of all these compounds were established by i.r., u.v., and 1H and 13C n.m.r. spectroscopy.
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Doi:10.1021/ja047498f
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(1980)
