Synthesis, Table of Contents Synthesis 2015; 47(07): 955-960DOI: 10.1055/s-0034-1379985 paper © Georg Thieme Verlag Stuttgart · New York Synthesis of 3-Ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one by Novel Palladium(II)-Catalyzed Cyclization and Ring-Closing Metathesis Subhash P. Chavan* Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India Email: sp.chavan@ncl.res.in , Ashok B. Pathak Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India Email: sp.chavan@ncl.res.in , Kailash P. Pawar Organic Chemistry Division, CSIR-NCL (National Chemical Laboratory), Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India Email: sp.chavan@ncl.res.in › Author Affiliations Recommend Article Abstract Buy Article All articles of this category Abstract Synthesis of 3-ethyl-4-methyl-1,5-dihydro-2H-pyrrol-2-one is described starting from commercially available allylamine and 4-methoxybenzylamine employing palladium-catalyzed cyclization or ring-closing metathesis as the key steps. Key words Key wordspyrrolinone - glimepiride - antidiabetic - metabolite - lactams - ring-closing metathesis - cyclization Full Text References References 1a Gurjar MK, Joshi RA, Chaudhuri SR, Joshi SV, Barde AR, Gediya LK, Ranade PV, Kadam SM, Naik SJ. Tetrahedron Lett. 2003; 44: 4853 1b Zhang H, Huang H, Zhou J, Zhao S, Huang W. Zhongguo Yaoke Daxue Xuebao 1999; 30: 163 2a Bishop JE, Nagy JO, O’Connell JF, Rapoport H. J. Am. Chem. Soc. 1991; 113: 8024 2b Sabido PM. G, Lightner DA. Monatsh. Chem. 2014; 145: 775 3a Deng Y, Zhong Y. Huaxi Yaoxue Zazhi 2000; 15: 289 3b Deng Y, Zhong Y, Tang W, Zhong Z. Zhongguo Yaowu Huaxue Zazhi 2000; 10: 134 3c Coffin AR, Roussell MA, Tserlin E, Pelkey ET. J. Org. Chem. 2006; 71: 6678 ; and references cited therein 4 Hayashi T, Hegedus LS. J. Am. Chem. Soc. 1977; 99: 7093 5 Chavan SP, Pathak AB, Kalkote UR. Synlett 2007; 2635 6a Chavan SP, Pasupathy K, Venkatraman MS, Kale RR. Tetrahedron Lett. 2004; 45: 6879 6b Chavan SP, Praveen C. Tetrahedron Lett. 2005; 46: 1939 6c Chavan SP, Thakkar M, Jogadand GF. J. Org. Chem. 2006; 71: 8986 6d Chavan SP, Sharma PS, Sivappa R, Kalkote UR. Tetrahedron Lett. 2006; 47: 9301 6e Chavan SP, Pathak AB, Dhawane AN, Kalkote UR. Synth. Commun. 2007; 37: 1503 6f Chavan SP, Dhawane AN, Kalkote UR. Tetrahedron Lett. 2007; 48: 965 6g Chavan SP, Pathak AB, Pandey A, Kalkote UR. Synth. Commun. 2007; 37: 3143 6h Li W.-R, Lin ST, Hsu N.-M, Chern M.-S. J. Org. Chem. 2002; 67: 4702 7 Aggarwal VK, Astle CJ, Rogers-Evans M. Org. Lett. 2004; 6: 1469 8 Giles M, Hadley MS, Gallagher T. Chem. Commun. 1990; 1047 9 Lee RA, McAndrews C, Patel KM, Ruesch W. Tetrahedron Lett. 1973; 965 10 Bryans JS, Chessums EA. N, Nathalie H, Parsons AF, Ghelfi F. Tetrahedron 2003; 59: 6221 For Pd(II)-mediated isomerization of olefins please see: 11a Sen A, Lai T.-W. Inorg. Chem. 1981; 20: 4036 11b Sen A, Lai T.-W. Inorg. Chem. 1984; 23: 3257 For palladium hydride mediated isomerization of olefins see: 11c Borszeky K, Mallat T, Baiker A. Catal. Lett. 1999; 59: 95 11d Crabtree RH. The Organometallic Chemistry of the Transition Metals. Wiley; New York: 1988: 188 11e Bartok M, Czombos J, Felfoldi K, Gera L, Gondos G, Molnar A, Notheisz F, Palinko I, Wittmann G, Zsigmond AG. Stereochemistry of Heterogeneous Metal Catalysis . Wiley; New York: 1985 12 Pikh ZG, Fedevich MD, Yatchishin II. Zh. Org. Khim. 1978; 1: 60 13 Hon Y.-S, Lin W.-C. Tetrahedron Lett. 1995; 36: 7693 14a Furstner A, Thiel OR, Ackermann L, Schanz H, Nolan PS. J. Org. Chem. 2000; 65: 2204 14b Rodriguez S, Castillo E, Carda M, Marco JA. Tetrahedron 2002; 58: 1185 14c Ackermann L, Ftirstner A, Weskamp T, Kohl FJ, Herrmann WA. Tetrahedron Lett. 1999; 40: 4787 15a Andreana PR, McLellan JS, Chen Y, Wang PG. Org. Lett. 2002; 4: 3875 15b D’Annibale A, Ciaralli L, Bassetti M, Pasquini C. J. Org. Chem. 2007; 72: 6067 16a Compound 13a: Riggi ID, Gastaldi S, Surzur J.-M, Bertrand MP. J. Org. Chem. 1992; 57: 6118 16b Compound 10a: Curti C, Ranieri B, Battistini L, Rassu G, Zambrano V, Pelosi G, Casiraghi G, Zanardi F. Adv. Synth. Catal. 2010; 352: 2011 16c Shao C, Yu H.-J, Wu N.-Y, Tian P, Wang R, Feng C.-G, Lin G.-Q. Org. Lett. 2011; 13: 788 16d Compound 13e: Kitagawa O, Aoki K, Inoue T, Taguchi T. Tetrahedron Lett. 1995; 36: 593 16e Compound 10e: Mathew J, Alink B. J. Org. Chem. 1990; 55: 3880 Supplementary Material Supplementary Material Supporting Information
