Unexpected Hydrazinolysis Behaviour of 1-Chloro-4-methyl-5H-pyridazino[4,5-b]indole and a Convenient Synthesis of New [1,2,4]-Triazolo[4’,3’:1,6]pyridazino[4,5-b]indoles

doi:10.3390/91000849

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Molecules 2004, 9(10), 849-859; doi:10.3390/91000849

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Unexpected Hydrazinolysis Behaviour of 1-Chloro-4-methyl-5H-pyridazino[4,5-b]indole and a Convenient Synthesis of New [1,2,4]-Triazolo[4’,3’:1,6]pyridazino[4,5-b]indoles

Hussein El-Kashef ¹, Abdelrahman A.H. Farghaly ¹, Norbert Haider ²^,* and Andrea Wobus ²

¹ Chemistry Department, Faculty of Science, Assiut University, 71516 Assiut, Egypt ² Department of Pharmaceutical Chemistry, University of Vienna, Althanstraße 14, A-1090 Vienna, Austria

* Author to whom correspondence should be addressed.

Received: 8 June 2004 / Accepted: 18 June 2004 / Published: 30 September 2004

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Abstract: Reaction of the title compound with hydrazine in the presence of air gives the 1-unsubstituted parent system via oxidative dehydrazination of the 1-hydrazino intermediate. The latter can be obtained in high yield by carrying out the hydrazinolysis step under inert gas, and it is smoothly converted into [1,2,4]-triazolo[4’,3’:1,6]pyridazino[4,5- b]indoles.

Keywords: Oxidative dehydrazination; pyridazine; indole; triazole.

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MDPI and ACS Style

El-Kashef, H.; Farghaly, A.A.H.; Haider, N.; Wobus, A. Unexpected Hydrazinolysis Behaviour of 1-Chloro-4-methyl-5H-pyridazino[4,5-b]indole and a Convenient Synthesis of New [1,2,4]-Triazolo[4’,3’:1,6]pyridazino[4,5-b]indoles. Molecules 2004, 9, 849-859.

AMA Style

El-Kashef H., Farghaly A.A.H., Haider N., Wobus A. Unexpected Hydrazinolysis Behaviour of 1-Chloro-4-methyl-5H-pyridazino[4,5-b]indole and a Convenient Synthesis of New [1,2,4]-Triazolo[4’,3’:1,6]pyridazino[4,5-b]indoles. Molecules. 2004; 9(10):849-859.

Chicago/Turabian Style

El-Kashef, Hussein; Farghaly, Abdelrahman A.H.; Haider, Norbert; Wobus, Andrea. 2004. "Unexpected Hydrazinolysis Behaviour of 1-Chloro-4-methyl-5H-pyridazino[4,5-b]indole and a Convenient Synthesis of New [1,2,4]-Triazolo[4’,3’:1,6]pyridazino[4,5-b]indoles." Molecules 9, no. 10: 849-859.

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