On the tautomerism of 2,1,3-benzothiadiazinone S,S-dioxide and related compounds

被引:6
作者
Castro, A [1 ]
Gil, C [1 ]
Martínez, A [1 ]
机构
[1] CSIC, Inst Quim Med, E-28006 Madrid, Spain
关键词
benzothiazines; tautomerism; theoretical studies; NMR;
D O I
10.1016/S0040-4020(99)00723-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Tautomerism of 2,1,3-benzothiadiazinone 2,2-dioxide and other related fused heterocyclic amides has been studied by means of experimental (H-1- and C-13-NMR) and theoretical (ab initio calculations) techniques. The synthesis and spectroscopic characterization of mono- and di-blocked derivatives was carried out. The results predict that the keto form is the most abundant tautomer in the gas phase, while the N1(H) hydroxy is the preferred one in solution and the solid state. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:12405 / 12410
页数:6
相关论文
共 20 条
[11]  
ELGUERO J, 1986, TAUTOMERISM HETEROCY
[12]   REGIOSELECTIVE LIPASE-MEDIATED ACYLATION-DEACYLATION IN THIADIAZINE DIACYCLONUCLEOSIDES [J].
ESTEBAN, AI ;
JUANES, O ;
MARTINEZ, A ;
CONDE, S .
TETRAHEDRON, 1994, 50 (48) :13865-13870
[13]  
Frisch M.J., 1995, GAUSSIAN 94 REVISION
[14]  
GOLDMAN RC, 1994, ANNU REP MED CHEM, V29, P155
[15]   Determination of the tautomeric equilibrium of Ψ-uridine in the basic solution [J].
Luyten, I ;
Pankiewicz, KW ;
Watanabe, KA ;
Chattopadhyaya, J .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :1033-1040
[16]   Benzothiadiazine dioxide acyclonucleosides as lead compounds for the development of new agents against human cytomegalovirus and varicella-zoster virus infections [J].
Martinez, A ;
Esteban, AI ;
DeClercq, E .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (08) :1031-1032
[17]   Novel potential agents for human cytomegalovirus infection: Synthesis and antiviral activity evaluation of benzothiadiazine dioxide acyclonucleosides [J].
Martinez, A ;
Esteban, AI ;
Castro, A ;
Gil, C ;
Conde, S ;
Andrei, G ;
Snoeck, R ;
Balzarini, J ;
De Clercq, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (07) :1145-1150
[18]  
MARTINEZ A, 1999, IN PRESS BIOORG MED
[19]  
MARTINEZ A, 1999, UNPUB J MED CHEM
[20]  
ONO M, 1977, J BIOCHEM-TOKYO, V81, P1247