Efficient synthesis of novel [1,3,4]thiadiazino[6,5-b]quinoxaline derivatives

Subject Areas :

Behnoush Ravizadeh ¹ , Mohsen Nikpour ² , Haman Tavakkoli ³

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Received: 2025-03-04 Accepted : 2025-04-25 Published : 2025-05-14

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. 

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