Reactions of 17-chloro-16-formylandrosta-5,16-diene with thiohydrazides of oxamic acids
Brief Communications
First Online:
Received:
- 65 Downloads
- 2 Citations
Abstract
Reactions of thiohydrazides of oxamic acids with 17-chloro-16-formylandrosta-5,16-diene give the corresponding thiohydrazones at the formyl group. Their subsequent reactions with alkali (het)arenethiolates yield 17-het(aryl)thio derivatives, being accompanied by cyclization of the thiooxalylhydrazone fragment into a 1,3,4-thiadiazole ring.
Key words
androstane thiohydrazides oxamic acids hydrazones sulfides 1,3,4-thiadiazoles heterocyclizationReferences
- 1.I. V. Zavarzin, V. V. Chertkova, I. S. Levina, E. I. Chernoburova, Russ. Chem. Rev., 2011, 80, 661 [Usp. Khim., 2011, 80, 693].CrossRefGoogle Scholar
- 2.A. V. Kamernitsky, E. I. Chernoburova, V. V. Chertkova, V. N. Yarovenko, I. V. Zavarzin, M. M. Krayushkin, Russ. Chem. Bull., 2006, 55, 2117 [Izv. Akad. Nauk, Ser. Khim., 2006, 2038].CrossRefGoogle Scholar
- 3.I. V. Zavarzin, A. V. Kamernitsky, V. V. Chertkova, E. I. Chernoburova, V. N. Yarovenko, M. M. Krayushkin, V. V. Kachala, ARKIVOC, 2008, iv, 62.CrossRefGoogle Scholar
- 4.D. G. Rivera, K. Peseke, I. Jomarrón, A. Montero, R. Molina, F. Coll, Molecules, 2003, 8, 444.CrossRefGoogle Scholar
- 5.H. S. Liu, H. L. Zheng, M. Ge, P. Xia, Y. Chen, Chinese Chem. Lett., 2011, 22, 757.CrossRefGoogle Scholar
- 6.M. M. Krayushkin, V. N. Yarovenko, I. V. Zavarzin, Russ. Chem. Bull., 2004, 53, 517 [Izv. Akad. Nauk, Ser. Khim., 2004, 491].CrossRefGoogle Scholar
Copyright information
© Springer Science+Business Media New York 2013