Journal of Heterocyclic Chemistry

Chemistry of thienopyridines. XIII. Selective formation of sulfones in Bi??and tricyclic Systems. Thieno [2, 3??b] pyridine 1, 1??dioxide as a dienophile

LH Klemm, RE Merrill

Index: Klemm,L.H.; Merrill,R.E. Journal of Heterocyclic Chemistry, 1972 , vol. 9, p. 293 - 298

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Citation Number: 22

Abstract

Abstract Bicyclic and tricyclic thienopyridines are converted into sulfones in 13-73% yield by means of acid-hypochlorite. The sulfone thieno [2, 3-b] pyridine 1, 1-oxide (Ib) undergoes Diels-Alder condensation with furan (both exo and endo products formed), anthracene, and naphthacene. Self-condensation of Ib occurs with elimination of sulfur dioxide to give 8-(3- pyridyl) quinoline (XV). The structure of XV was established by means of pmr and a ...