【结 构 式】 |
【分子编号】34452 【品名】2lambda(6),1,3-benzothiadiazine-2,2,4(1H,3H)-trione 【CA登记号】 |
【 分 子 式 】C7H6N2O3S 【 分 子 量 】198.20232 【元素组成】C 42.42% H 3.05% N 14.13% O 24.22% S 16.18% |
合成路线1
该中间体在本合成路线中的序号:(II)Benzothiadiazine dioxide (II) was prepared by cyclization of methyl anthranylate (I) with sulfamoyl chloride, followed by aqueous NaOH. After silylation of (II) by means of hexamethyldisilazane, alkylation with benzyloxymethyl acetate (III) in the presence of boron trifluoride etherate produced the 3-(benzyloxymethyl)benzothiazine (IV). Further alkylation of (IV) with benzyl bromide in aqueous NaHCO3 furnished the title compound.
【1】 Esteban, A.I.; Martinez, A.; De Clercq, E.; Benzothiadiazine dioxide acyclonucleosides as lead compounds for the development of new agents against human cytomegalovirus and varicella-zoster virus infection. Bioorg Med Chem Lett 1997, 7, 8, 1031. |
【2】 Martinez, A.; et al.; Novel potential agents for human cytomegalovirus infection: Synthesis and antiviral activity evaluation of benzothiadiazine dioxide acyclonucleosides. J Med Chem 1999, 42, 7, 1145. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
12912 | 1-(Bromomethyl)benzene; Alpha-bromotoluene | 100-39-0 | C7H7Br | 详情 | 详情 | |
40598 | amidosulfonoyl chloride | 7778-42-9 | H2ClNO2S | 详情 | 详情 | |
(I) | 11161 | methyl 2-aminobenzoate; Methyl anthranilate | 134-20-3 | C8H9NO2 | 详情 | 详情 |
(II) | 34452 | 2lambda(6),1,3-benzothiadiazine-2,2,4(1H,3H)-trione | C7H6N2O3S | 详情 | 详情 | |
(III) | 34453 | (benzyloxy)methyl acetate | C10H12O3 | 详情 | 详情 | |
(IV) | 34454 | 3-[(benzyloxy)methyl]-2lambda(6),1,3-benzothiadiazine-2,2,4(1H,3H)-trione | C15H14N2O4S | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(II)Benzothiadiazine S,S-dioxide (II) was obtained by a two-step condensation of methyl anthranylate (I) and sulfamoyl chloride following a reported procedure (1). The alkylation of (II) with 3,4-dichlorobenzyl chloride (III) in the presence of NaHCO3 furnished the title compound.
【1】 J Am Chem Soc 1962, 84, 1994-2000. |
【2】 Castro, A.; Gil, C.; Martinez, A.; et al.; Benzyl derivatives of 2,1,3-benzo- and benzothieno[3,2-a]thiadiazine 2,2-dioxides: First phosphodiesterase 7 inhibitors. J Med Chem 2000, 43, 4, 683. |