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Chemistry of thienopyridines. XXXVIII . Diels‐Alder reactions of thienopyridine sulfones. Part 2
Author(s) -
Klemm L. H.,
Sur Sandip K.,
Louris John N.,
Tran Long K.,
Yee Sidney,
Hamilton Steven R.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270638
Subject(s) - chemistry , anthracene , medicinal chemistry , cyclopentadiene , sulfur dioxide , pyridine , thiophene , quinoline , thienopyridine , yield (engineering) , derivative (finance) , organic chemistry , catalysis , biochemistry , materials science , aspirin , economics , financial economics , metallurgy , clopidogrel
Thieno[3,2‐ b ]pyridine 1,1‐dioxide ( 2 ) undergoes Diels‐Alder condensation with the dienophiles cyclopentadiene, anthracene, and naphthacene in a manner analogous to its isomer thieno[2,3‐ b ]pyridine 1,1‐dioxide ( 1 ). Compound 2 dimerizes in refluxing xylene with the loss of sulfur dioxide plus either the loss or transfer of hydrogen to give a small yield ( ca . 2%) of pyrido[2′,3′:4,5]thieno[3,2‐ f ]quinoline 7,7‐dioxide ( 7 ) and its 5,6‐dihydro derivative 12 . Formation of 7 and 12 are compared and contrasted with products reported from dimerization of 1 and of benzo[ b ]thiophene 1,1‐dioxide and its derivatives.