Molecules 2003, 8(5), 444-452; doi:10.3390/80500444

Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives

1, 2,* email, 1, 3, 3 and 1
Received: 16 April 2003; in revised form: 8 May 2003 / Accepted: 9 May 2003 / Published: 31 May 2003
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: The synthesis of steroidal heterocycles containing the pyrazole and pyrimidine ring fused to the 16,17-position of the steroid nucleus is reported. Androstenolone acetate (1) reacted with carbon disulfide, iodomethane and sodium hydride to furnish 3β-acetoxy-16-[bis(methylthio)methylene]-5-androst-5-en-17-one (2). The reactions of 2 with hydrazine hydrate and methylhydrazine afforded the 5’-methylthio- pyrazolo[4’,3’:16,17]androst-5-en-3β-ols 3a and 3b, respectively. Treatment of 2 with amidinium, guanidinium, and isothiuronium salts in the presence of sodium methoxide yielded the 6’-methoxy-pyrimido[5’,4’:16,17]androst-5-en-3β-ols (4a-4e).
Keywords: Androstenolone; steroidal heterocycles; push-pull alkenes; pyrazoles; pyrimidines
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MDPI and ACS Style

Rivera, D.G.; Peseke, K.; Jomarrón, I.; Montero, A.; Molina, R.; Coll, F. Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives. Molecules 2003, 8, 444-452.

AMA Style

Rivera DG, Peseke K, Jomarrón I, Montero A, Molina R, Coll F. Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives. Molecules. 2003; 8(5):444-452.

Chicago/Turabian Style

Rivera, Daniel G.; Peseke, Klaus; Jomarrón, Isabel; Montero, Alina; Molina, Reinaldo; Coll, Francisco. 2003. "Synthesis of New Pyrazole and Pyrimidine Steroidal Derivatives." Molecules 8, no. 5: 444-452.

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