新产品编号:718737

Chemical Name: 1-(2,2-Dimethyl-6-nitro-2,3-dihydro-4H-1,4-benzothiazin-4-yl)-2-propanone
CAS No. 265994-74-9
项目整合开发状态: Biological Testing
项目研究机构: Yamanouchi (Originator)
合成路线:Alkylation of 2,4-dinitrothiophenol (I) with 2-bromoisobutyrate (II) and K2CO3 in DMF yields thioether (III),which is then subjected to reduction with Fe/HCl in EtOH/H2O,followed by ring closure with refluxing NaOH,to give benzothiazine derivative (IV).Conversion of amino compound (IV) into nitro derivative (V) is then performed via Sandmeyer reaction by first treatment with NaNO2/H2SO4 in H2O,followed by reaction with NaHCO3,NaNO2,CuSO4 and Cu2O in H2O.N-Alkylation of (V) with chloroacetone (VI) and K2CO3 in DMF provides (VII),which is finally converted into the target compound by reduction with BH3-THF complex in THF,followed by Swern oxidation with DMSO and oxalyl chloride in CH2Cl2.
📌 参考资料/链接:
参考文献标题:Novel potassium channel openers.Part 4: Transformation of the 1,4-benzoxazine skeleton into 1,4-benzothiazine,1,2,3,4-tetrahydroquinoline,1,2,3,4-tetrahydroquinoxaline,indoline,and 1,5-benzoxazepine
文献作者:Matsumoto,Y.; Tsuzuki,R.; Matsuhisa,A.; Yamagiwa,Y.; Yanagisawa,I.; Shibanuma,T.; Nohira,H.
参考来源:Bioorg Med Chem 2000,8(2),393