Thermolysis of thiophenedicarboxylic acid anhydrides as a route to five-membered hetarynes

MG Reinecke, JG Newsom…

Index: Reinecke, Manfred G.; Newsom, James G.; Chen, Lao-Jer Journal of the American Chemical Society, 1981 , vol. 103, # 10 p. 2760 - 2769

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Citation Number: 33

Abstract

Abstract: Flow vacuum thermolysis (FVT) of the anhydrides of thiophene-2, 3-(5) and-3, 4- dicarboxylic acid (6) and of thianaphthene-2, 3-dicarboxylic acid (7) in the presence of thiophene, 1, 3-cyclohexadiene, or benzene gave thianaphthene (Ma), presumably by aromatization of an intermediate Diels-Alder adduct of the diene traps and the aryne 2, 3- didehydrothiophene (8). A similar rationale explains the formation of dibenzothiophene ...

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Structure-based design, synthesis, and biological evaluation...

[Kim, Sun Hee; Tran, Martin T.; Ruebsam, Frank; Xiang, Alan X.; Ayida, Benjamin; McGuire, Helen; Ellis, David; Blazel, Julie; Tran, Chinh V.; Murphy, Douglas E.; Webber, Stephen E.; Zhou, Yuefen; Shah, Amit M.; Tsan, Mei; Showalter, Richard E.; Patel, Rupal; Gobbi, Alberto; LeBrun, Laurie A.; Bartkowski, Darian M.; Nolan, Thomas G.; Norris, Daniel A.; Sergeeva, Maria V.; Kirkovsky, Leo; Zhao, Qiang; Han, Qing; Kissinger, Charles R. Bioorganic and Medicinal Chemistry Letters, 2008 , vol. 18, # 14 p. 4181 - 4185]