Synthesis of N-aryl substituted 4H-1,4-benzothiazine 1,1-dioxide 2-carboxylic acid-esters

被引:4
|
作者
Lopez, SE
Charris, J
Urdaneta, N
Lobo, G
机构
[1] Univ Simon Bolivar, Dept Quim, Lab Quim Organ 210, Caracas 1080A, Venezuela
[2] Cent Univ Venezuela, Fac Farm, Lab Sintesis Organ, Caracas 1051, Venezuela
关键词
4H-1,4-benzothiazine-1,1-dioxide; N-aryl-phenylsulfonylacrylates; cyclization reaction;
D O I
10.1080/10426509808045484
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A group of N-aryl substituted 14-benzothiazine-1,1-dioxide-2 carboxylic acid esters is reported. This is the first example of N-aryl-derivatives of the 4H-1,4-benzothiazine nucleus; the key step is the cyclization of N-aryl-phenylsulfonyl-acrylates 4-8 using potassium carbonate in acetonitrile/18-crown-6-ether to the corresponding title compounds in moderate yields.
引用
收藏
页码:53 / 61
页数:9
相关论文
共 50 条
  • [1] An improved procedure for the preparation of N-aryl substituted 4H-1,4-benzothiazine 1,1-dioxide derivatives
    Lopez, SE
    Godoy, MV
    Urdaneta, N
    Rosales, M
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2000, 156 : 69 - 80
  • [2] 13C NMR spectral characterization of N-aryl-substituted 4H-1,4-benzothiazine 1,1-dioxide derivatives
    López, SE
    Godoy, MV
    Charris, J
    Urdaneta, N
    Salazar, J
    Puig, AI
    MAGNETIC RESONANCE IN CHEMISTRY, 2000, 38 (05) : 386 - 387
  • [3] SYNTHESIS OF 4H-1,4-BENZOTHIAZINE 1-OXIDE AND 1,1-DIOXIDE - ANALOGS OF QUINOLONE ANTIBACTERIAL AGENTS
    CULBERTSON, TP
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (07) : 1701 - 1703
  • [4] High yield synthesis of 4H-1,4-benzothiazine-1,1-dioxide derivatives
    De Montis, Stefania
    Fattuoni, Claudia
    Cadoni, Enzo
    Cabiddu, Maria G.
    Usai, Michele
    Cabiddu, Salvatore
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 45 (05) : 1445 - 1449
  • [5] CYCLIC SULFONES .6. 4H-1,4-BENZOTHIAZINE-1,1-DIOXIDE
    PAGANI, G
    PAGANI, SB
    TETRAHEDRON LETTERS, 1968, (09) : 1041 - &
  • [6] A microwave induced cyclisation of α-phenylsulfonyl-enaminoacrylates for the preparation of 4-aryl-4H-1,4-benzothiazine 1,1-dioxide derivatives
    López, SE
    Salazar, J
    Rebollo, O
    Restrepo, J
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 42 (05) : 1007 - 1010
  • [7] 4H-1,4-THIAZINE 1,1-DIOXIDE
    NOLAND, WE
    DEMASTER, RD
    ORGANIC SYNTHESES, 1988, 50-9 : 976 - 979
  • [8] Microwave-assisted synthesis of quinolones and 4H-1,4-benzothiazine 1,1-dioxides
    Charris, J
    Barazarte, A
    Domínguez, J
    Gamboa, N
    JOURNAL OF CHEMICAL RESEARCH, 2005, (01) : 27 - 28
  • [9] Synthesis, Spectral Characterization and Antioxidative Evaluation of Substituted 4H-1,4-Benzothiazine and Their Sulfones
    Gautam, Naveen
    Sharma, Meenakshi
    Gautam, Vibha
    Sharma, M. K.
    Gautam, D. C.
    ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (07) : 5380 - 5388
  • [10] THE SYNTHESIS OF FLUORINATED 4H-1,4-BENZOTHIAZINE-2-CARBOXYLIC ACID 1,1-DIOXIDES-THIONATED ANALOGS OF PEFLOXACIN
    VYSOKOV, VI
    CHARUSHIN, VN
    AFANASYEVA, GB
    CHUPAKHIN, ON
    MENDELEEV COMMUNICATIONS, 1993, (04) : 159 - 160