Synthesis of Novel Dispiro 1,4-Benzothiazine Hybrid Heterocycles Through 1,3-Dipolar Cycloaddition
作者： Karuppiah Malathi , Veerappan Jeyachandran , Karumpan Kalaiselvan , Raju Ranjith Kumar , None
DOI: 10.1080/00397911.2014.965329
关键词: Stereoselectivity 、 Cycloaddition 、 Benzothiazine 、 Chemistry 、 1,3-Dipolar cycloaddition 、 Azomethine ylide 、 Organic chemistry 、 Pyrrolidine
摘要: AbstractThe 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the reaction acenaphthylene-1,2-dione or isatins and α-amino acids to (E)-methyl/ethyl 2-(3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazin-2-ylidene)acetate led stereoselective formation novel dispiro 1,4-benzothiazine hybrid heterocycles good yields.
sci-hub.se 参考文章(17)
Garima Choudhary, Rama Krishna Peddinti, Introduction of a clean and promising protocol for the synthesis of β-amino-acrylates and 1,4-benzoheterocycles: an emerging innovation Green Chemistry. ,vol. 13, pp. 3290- 3299 ,(2011) , 10.1039/C1GC15701A
Brent K Warren, Edward E Knaus, Pyridine and reduced pyridine analogues of 10H-pyrido[3,4-b][1,4]benzothiazines with analgesic activity European Journal of Medicinal Chemistry. ,vol. 22, pp. 411- 415 ,(1987) , 10.1016/0223-5234(87)90028-6
Yves Jacquot, Laurent Bermont, Hervé Giorgi, Bernard Refouvelet, Gerard.L Adessi, Edwige Daubrosse, Alain Xicluna, Substituted benzopyranobenzothiazinones. Synthesis and estrogenic activity on MCF-7 breast carcinoma cells. European Journal of Medicinal Chemistry. ,vol. 36, pp. 127- 136 ,(2001) , 10.1016/S0223-5234(00)01207-1
Fausto Schiaffella, Antonio Macchiarulo, Lara Milanese, Anna Vecchiarelli, Renata Fringuelli, Novel ketoconazole analogues based on the replacement of 2,4-dichlorophenyl group with 1,4-benzothiazine moiety: Design, synthesis, and microbiological evaluation Bioorganic & Medicinal Chemistry. ,vol. 14, pp. 5196- 5203 ,(2006) , 10.1016/J.BMC.2006.04.004
Katsutoshi Hasegawa, Shosuke Ito, Shigeki Inoue, Kazumasa Wakamatsu, Hiroyuki Ozeki, Isao Ishiguro, Dihydro-1,4-benzothiazine-6,7-dione, the ultimate toxic metabolite of 4-S-cysteaminylphenol and 4-S-cysteaminylcatechol Biochemical Pharmacology. ,vol. 53, pp. 1435- 1444 ,(1997) , 10.1016/S0006-2952(97)00075-0
Magid A. Abou-Gharbia, Peter H. Doukas, Synthesis of Tricyclic Arylspiro Compounds as Potential Antileulemic and Anticonvulsant Agents Heterocycles. ,vol. 12, pp. 637- ,(1979) , 10.3987/R-1979-05-0637
Olayinka Oyewale Ajani, Functionalized 1,4-benzothiazine: a versatile scaffold with diverse biological properties. Archiv Der Pharmazie. ,vol. 345, pp. 841- 851 ,(2012) , 10.1002/ARDP.201200140
K. Lundahl, J. Schut, J. L. M. A. Schlatmann, G. B. Paerels, A. Peters, Synthesis and antiviral activities of adamantane spiro compounds. 1. Adamantane and analogous spiro-3'-pyrrolidines. Journal of Medicinal Chemistry. ,vol. 15, pp. 129- 132 ,(1972) , 10.1021/JM00272A003
Susan A. Coughlin, Deborah W. Danz, Ronald G. Robinson, Kristina M. Klingbeil, Mark P. Wentland, Thomas H. Corbett, William R. Waud, Leonard A. Zwelling, Elizabeth Altschuler, Elise Bales, James B. Rake, Mechanism of action and antitumor activity of (S)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyridol [1,2,3-de]-[1,4]benzothiazine-6-carboxylic acid (WIN 58161) Biochemical Pharmacology. ,vol. 50, pp. 111- 122 ,(1995) , 10.1016/0006-2952(95)00016-S
Milton J. Kornet, Alan P. Thio, Oxindole-3-spiropyrrolidines and -piperidines. Synthesis and local anesthetic activity. Journal of Medicinal Chemistry. ,vol. 19, pp. 892- 898 ,(1976) , 10.1021/JM00229A007