原创力文档regioselective synthesis of novel n2- and n4-substituted 7-methylpyrazolo[4,5-e][1,2,4]thiadiazines特定选择的合成新颖的n2 - n4-substituted 7-methylpyrazolo(4,5 e)(1、2、4)thiadiazines.pdfVIP
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regioselective synthesis of novel n2- and n4-substituted 7-methylpyrazolo[4,5-e][1,2,4]thiadiazines特定选择的合成新颖的n2 - n4-substituted 7-methylpyrazolo(4,5 e)(1、2、4)thiadiazines
Molecules 2006, 11, 827-836
molecules
ISSN 1420-3049
Full Paper
Regioselective Synthesis of Novel N - and N -Substituted 7-
2 4
Methylpyrazolo[4,5-e][1,2,4]thiadiazines
Xinyong Liu 1,*, Renzhang Yan 1, Niangen Chen 1, Wenfang Xu 1, Maria Teresa Molina 2 and
2
Salvador Vega
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; Xinyong Liu, E-mail: xinyongl@;
Tel: (+86)-531-8382005; Fax: (+86)-531-8382264
Received: 5 October 2006; in revised form: 22 October 2006/ Accepted: 23 October 2006 /
Published: 1 November 2006
Abstract: The new compound 7-methylpyrazolo[4,5-e][1,2,4]thiadiazin-3(2H,4H)-one
1,1-dioxide (5) was synthesized and its novel mono N - or N -substituted derivatives 6
2 4
and 7 were prepared by regioselective N-alkylation of 5 with different molar ratios of
NaH and alkyl halides. Based on the regioselective alkylation conditions found a facile
one-pot synthesis of N ,N -disubstituted pyrazolo[4,5-e][1,2,4] thiadiazines 8 was
2 4
developed. 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
Introdu
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