Synlett, Table of Contents Synlett 2012; 23(18): 2639-2642DOI: 10.1055/s-0032-1317381 letter © Georg Thieme Verlag Stuttgart · New YorkOne-Pot Thiourea Formation–Palladium-Catalyzed Cyclization Sequence to 3,4-Dihydro-2H-1,3-benzothiazine-2-imines from 2-Halo N-Methylbenzylamine – Scope and Limitations Franck Lach* AstraZeneca, Parc Industriel Pompelle, Chemin de Vrilly, BP 1050-51698 Reims, Cedex 2, France Fax: +33(3)26616842 Email: franck.lach@astrazeneca.com Email: franck_lach@hotmail.com› Author AffiliationsRecommend Article Abstract Buy Article All articles of this category Abstract A practical synthesis of 3,4-dihydro-3-methyl-2H-1,3-benzothiazine-2-imine via intramolecular palladium-catalyzed C–S bond formation is presented and exemplified for both alkyl- and arylisothiocyanates. Key words Key wordspalladium - heterocycles - sulfur - ring closure - catalysis Full Text References References and Notes 1 Senthilvelan A, Ramanakrishnan VT. Tetrahedron Lett. 2002; 5119 2 Voigt E, Meier H. Angew. Chem., Int. Ed. Engl. 1976; 15: 117 3 Groelsch D, Niedermann HP, Meier H. Chem. Ber. 1994; 127: 955 4 Mizuhara T, Oishi S, Fujii N, Ohnon H. J. Org. Chem. 2010; 75: 265 For references on the thermal synthesis of 2-amino benzothiazoles via base-promoted cyclization of o-bromophenylthiourea and the rationale about factors involved in such a SNAr activation, see: 5a Feng E, Huang H, Zhou Y, Ye D, Jiang H, Liu H. J. Comb. Chem. 2010; 12: 422 5b Ding Q, Huang X, Wu J. J. Comb. Chem. 2009; 11: 1047 6 Orain D, Blumstein A, Tasdelen E, Haessig S. Synlett 2008; 2433 7 Hardy S, Martin SF. Org. Lett. 2011; 13: 3102 8 Ikawa T, Barder TE, Biscoe MR, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 13001 9 Fujita K, Yamashita M, Puschmann F, Alvarez-Falcon M, Incarvito CD, Hartwig JF. J. Am. Chem. Soc. 2006; 128: 9044 10 For a general procedure and spectroscopic data for final compounds 3a–j, see the Supporting Information. 11 Hammann BC, Hartwig JF. J. Am. Chem. Soc. 1998; 120: 7369 12 Suparabhorn S, Lange S, Chen W, Xiao J. J. Mol. Catal. A 2003; 196: 125 13 Singer RA, Dore M, Sieser JE, Berliner MA. Tetrahedron Lett. 2006; 47: 3727 14 Kotecki BJ, Fernando DP, Haight AR, Lukin KA. Org. Lett. 2009; 11: 947 15 McLaughlin M, Palucki M, Davies IW. Org. Lett. 2006; 8: 3311 16 Littke AF, Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176 17 Hartwig JF. Pure Appl. Chem. 1999; 71: 1417 Supplementary Material Supplementary Material Supporting Information
