Efficient synthesis of novel [1,3,4]thiadiazino[6,5-b]quinoxaline derivatives
محورهای موضوعی : Organic and Inorganic synthesisBehnoush 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
کلید واژه: methylhydrazine, [1, 3, 4]thiadiazino[6, 5-b]quinoxaline, ,
چکیده مقاله :
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.
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.
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