Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York One-Step Synthesis of Thieno[3,2-b]thiophene 1,1-Dioxide Derivatives Claudia Fattuoni*, Michele Usai, M. Grazia Cabiddu, Enzo Cadoni, Stefania De Montis, Salvatore CabidduDipartimento di Scienze Chimiche, Università di Cagliari, Cittadella Universitaria di Monserrato, SS. 554, Bivio per Sestu, 09042 Monserrato (CA), ItalyFax: +39(070)6754388; e-Mail: cfattuon@unica.it; Recommend Article Abstract Buy Article All articles of this category Abstract A rapid, one-step synthesis of thieno[3,2-b]thiophene 1,1-dioxide derivatives using direct bimetalation of 3-(methylsulfonyl)thiophene and ring closure with esters is described. Two iterative, one-pot monometalations of the same substrate allowed bifunctionalization with either equal or different groups, after electrophilic quenching. Key words thienothiophenes - metalations - lithiation - cyclizations - carbanions Full Text References References 1 Litvinov VP. Adv. Heterocycl. Chem. 2006, 90: 125 2 Comel A. Sommen G. Kirsch G. Mini-Rev. Org. Chem. 2004, 1: 367 3 Fuller LS. Iddon B. Smith KA. J. Chem. Soc., Perkin Trans. 1 1997, 3465 4 Nenajdenko VG. Sumerin VV. Chernichenko KY. Balenkova ES. Org. Lett. 2004, 6: 3437 5 Leriche P. Raimundo J.-M. Turbiez M. Monroche V. Allain M. Sauvage F.-X. Roncali J. Frère P. Skabara PJ. J. Mater. Chem. 2003, 13: 1324 6 Prugh JD. Hartman GD. Mallorga PJ. McKeever BM. Michelson SR. Murcko MA. Schwam H. Smith RL. Sondey JM. Springer J. Sugrue MF. J. Med. Chem. 1991, 34: 1805 7 Litvinov VP. Gol’dfarb YaL. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1963, 2011 8 Litvinov VP. Fraenkel G. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1968, 1729 9 De Jong F. Janssen M. J. Chem. Soc., Perkin Trans. 2 1972, 572 10a Litvinov VP. Gol’dfarb YaL. Adv. Heterocycl. Chem. 1976, 19: 123 10b Choi KS. Sawada K. Dong H. Hoshino M. Nakayama J. Heterocycles 1994, 38: 143 10c Capozzi G. De Sio F. Menichetti S. Nativi C. Pacini PL. Synthesis 1994, 521 11a Gronowitz S. Ark. Kemi 1958, 13: 269 11b Brandsma L. Verkruijsse H. In Preparative Polar Organometallic Chemistry 1 Springer-Verlag; Berlin: 1987. Chap. 5. 12 Fattuoni C. Usai M. Cabiddu MG. Cadoni E. De Montis S. Sotgiu F. Cabiddu S. J. Heterocycl. Chem. in press 13 Bongini A. Savoia D. Umani-Ronchi A. J. Organomet. Chem. 1976, 112: 1 14 Duhamel L. Plaquevent JC. J. Org. Chem. 1979, 44: 3404
