Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York A New Facile Synthesis of exo-Methylene 3,1-Benzothiazines Michael Schmittel*, Atul Mahajan, Jens-Peter SteffenFB 8 - OC1, Chemie-Biologie, Universität Siegen, Adolf-Reichwein-Str., 57068 Siegen, GermanyFax: +49(271)7403270; e-Mail: schmittel@chemie.uni-siegen.de; Recommend Article Abstract Buy Article All articles of this category Abstract A facile synthesis of exo-methylene 3,1-benzothiazines from ortho-alkynylated aniline 1 with alkyl or aryl isothiocyanates is described. The reaction can be set up both in a discontinuous or continuous process, the latter protocol explored with a Cellular Process Chemistry (CPC) reactor. Key words thiazine - cyclization - continuous process Full Text References References 1 Millonig RC. Goldlust MB. Maguire WE. Rubin B. Schulze E. Wojnar RJ. Turkheimer AR. Schreiber WF. Brittain RJ. J. Med. Chem. 1973, 16: 780 2 Hari A. Miller BL. Org. Lett. 2000, 2: 3667 3 Hull R. van den Broek P. Swain ML. J. Chem. Soc., Perkin Trans. 1 1975, 922 For the synthesis of 4-aryl and unsubstituted 4H-3,1-benzothiazines. 4a Nishio T. J. Org. Chem. 1997, 62: 1106 4b El-Desoky SI. Kandeel EM. Abd-el-Rahman AH. Schmidt RR. J. Heterocycl. Chem. 1999, 36: 153 4c Besson T. Guillaumet G. Lamazzi C. Ress CW. Synlett 1997, 704 5 Fathalla WM. Pazdera P. Molecules 2000, 7: 96 6a Ebel M. Bull. Soc. Chim. Fr. 1971, 187 6b Lohse C. Pedersen CT. Ebel M. Callendret R. J. Chem. Soc. Perkin Trans. 1 1978, 1432 6c Latif N. Zeid IF. Mishriky N. Assad FM. Rec. Trav. Chim. Pays-Bas 1981, 100: 95 7 Xiao W.-J. Alper H. J. Org. Chem. 1999, 64: 9646 8 Thorand S. Krause N. J. Org. Chem. 1998, 63: 8551 9 Taghavi-Moghadam S. Kleemann A. Golbig KG. Org. Proc. Res. Dev. 2001, 5: 652 10 For additional information: www.cpc-net.com.
