Efficient synthesis of novel [1,3,4]thiadiazino[6,5-b]quinoxaline derivatives
Subject Areas :Behnoush Ravizadeh 1 , mohsen Nikpour 2 * , Haman Tavakkoli 3
1 - Islamic Azad University, Ahvaz Branch,IRAN
2 - Department of Chemistry, Islamic Azad University of Ahvaz
3 - Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran
Keywords: methylhydrazine, [1, 3, 4]thiadiazino[6, 5-b]quinoxaline, ,
Abstract :
Reaction of 2,3-dichloroquinoxaline with hydrazine and methylhydrazine gave 2-chloro-3-hydrazinyl quinoxaline and 2-chloro-3-(1-methylhydrazinyl) quinoxaline respectively in ethanol at room temperature. Condensation of 2-chloro-3-hydrazinyl quinoxaline and 2-chloro-3-(1-methylhydrazinyl) quinoxaline with carbon disulfide, trimethylamine and alkylhalides achieved a group of 3-(alkylsulfanyl) -1H-[1,3,4]thiadiazino[6,5-b]quinoxaline and 1-methyl-3-(alkylsulfanyl)-1H-[1,3,4]thiadiazino[6,5-b]quinoxaline respectively. Solvent effect of methanol and acetonitrile on this reaction and the spectral data is discussed. Fused [1,3,4]thiadiazines are a well known class of heterocycles. Among this class, [1,3,4]thiadiazino[6,5-b]quinoxaline have attracted less attention. There are a few routes for the preparation of this valuable compounds including; ring expansion of 3-amino-2-iminothiazolo[4,5-b]quinoxaline [1] and the cyclization of N-alkylazinium cations or 2,3-dichloroquinoxaline with bifunctional nuclephiles such as thiohydrazides and dithizone [2−4], which the last route utilized expensive reagents for the preparation of few derivatives.
[1] Y. A. Ammar, I. M. Ismail, A. M. El- Sharief, Y. A. Mohamed and R. M. Amer, J. Ind. Chem. Soc. 1989, 66, 124.
[2] V. G. Baklykov, V. N. Charushin, O. N. Chupakhin and V. N. Droazd; Cyclization of N-Alkylazinium Cations with Bifunctional Nucleophiles. Part 21. Regioisomeric 1,3,4-Thiadiazino(5,6-b)quinoxalines; Khim. Getrosikl. Soedin. 1987, 4, 557-561.
[3] A. Ghaemi, F. Mohave, A. Farhadi, M. A. Takassi, H. Tavakkoli; Hydrothermal synthesis of mesoporous cobalt ferrite by ionic liquid-assisted process; catalytic performance, morphology, and magnetic studies; J. Aust. Ceram. Soc. 2021, 57, 1321–1330.
[4] A. J. Elliot and M. S. Gibson; Hydrazides and Thiohydrazides as Sources of Condensed Oxadiazines and Thiadiazines, Including Novel Azo Derivatives Based on Dithizone; J. Org. Chem. 1980, 45, 3677-3681.
[5] M. Bakavoli, M. Nikpour and M. Rahimizadeh; Synthesis of Some New 3-Alkylthio Derivatives of 1-Phenyl-1H-[1,3,4]thiadiazino[5,6-b]quinoxalines; Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 2265-2268.
[6] M. Nikpour, M. Bakavoli, M. Rahimizadeh, A. J. Sabbaghian and M. R. Bigdeli; Synthesis of Some New 3-Alkylthio Derivatives of 1-Phenyl-1H-[1,3,4]thiadiazino[5,6-b]quinoxalines; Mendel. Commun. 2008, 18, 284-285.
[7] M. Nikpour, M. Gholami and E. Molashahi; An Efficient Route to Pyridazino[4, 3-e][1, 3, 4]thiadiazines; J. Heterocycl. Chem. 2016, 53, 1457-1460.
[8] M. Rahimizadeh, M. Nikpour and M. Bakavoli; New Route to Pyrimido[4,5- e][1,3,4]thiadiazine Derivatives; J. Heterocycl. Chem. 2007, 44, 463-465.
[9] R. Sarges, H. R. Howard, R. G. Browne, L. A. Lebel, P. A. Seymour and B. K. Koe; 4-Amino[ 1,2,4]triazolo[4,3-a Iquinoxalines. A Novel Class of Potent Adenosine Receptor Antagonists and Potential Rapid-Onset Antidepressants; J. Med. Chem. 1990, 33, 2240-2254.