Regioselective Synthesis of Novel N2- and N4-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]thiadiazines

doi:10.3390/11110827

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Molecules 2006, 11(11), 827-836; doi:10.3390/11110827

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Regioselective Synthesis of Novel N₂- and N₄-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]thiadiazines

Xinyong Liu ¹^,* , Renzhang Yan ¹, Niangen Chen ¹, Wenfang Xu ¹, Maria T. Molina ² and Salvador Vega ²

¹ Institute of Medicinal Chemistry, School of Pharmacy, Shandong University, Jinan 250012, P.R. China ² Instituto de Quimica Medica (CSIC), c/Juan de la Cierva, 3, 28006 Madrid, Spain

* Author to whom correspondence should be addressed.

Received: 5 October 2006; in revised form: 22 October 2006 / Accepted: 23 October 2006 / Published: 1 November 2006

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Abstract: The new compound 7-methylpyrazolo[4,5-e][1,2,4]thiadiazin-3(2H,4H)-one1,1-dioxide (5) was synthesized and its novel mono N₂- or N₄-substituted derivatives 6and 7 were prepared by regioselective N-alkylation of 5 with different molar ratios ofNaH and alkyl halides. Based on the regioselective alkylation conditions found a facileone-pot synthesis of N₂,N₄-disubstituted pyrazolo[4,5-e][1,2,4] thiadiazines 8 wasdeveloped. The structures of the newly synthesized compounds were confirmed by IR,¹H-NMR, ¹³C-NMR and MS spectral analysis.

Keywords: Pyrazolothiadiazines; regioselectivity; synthesis; alkylation; one-pot reaction

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MDPI and ACS Style

Liu, X.; Yan, R.; Chen, N.; Xu, W.; Molina, M.T.; Vega, S. Regioselective Synthesis of Novel N₂- and N₄-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]thiadiazines. Molecules 2006, 11, 827-836.

AMA Style

Liu X., Yan R., Chen N., Xu W., Molina M.T., Vega S. Regioselective Synthesis of Novel N₂- and N₄-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]thiadiazines. Molecules. 2006; 11(11):827-836.

Chicago/Turabian Style

Liu, Xinyong; Yan, Renzhang; Chen, Niangen; Xu, Wenfang; Molina, Maria T.; Vega, Salvador. 2006. "Regioselective Synthesis of Novel N₂- and N₄-Substituted 7-Methylpyrazolo[4,5-e][1,2,4]thiadiazines." Molecules 11, no. 11: 827-836.

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