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An alternative route to 2 H ‐naphtho[1,2‐ b ]thiete and its cycloaddition products
Author(s) -
Rumpf Norbert,
Gröschl Dieter,
Meier Herbert,
Oniciu Daniela C.,
Katritzky Alan R.
Publication year - 1998
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.5570350648
Subject(s) - flash vacuum pyrolysis , chemistry , cycloaddition , pyrolysis , sulfur , yield (engineering) , ring (chemistry) , nitrogen , extrusion , medicinal chemistry , flash (photography) , organic chemistry , catalysis , metallurgy , art , materials science , visual arts
2‐(1 H ‐Benzotriazol‐1‐ylmethyl)‐1‐naphthalenol ( 1 ) can be transformed in high yields to the corresponding thiol 4 . Flash vacuum pyrolysis of 4 leads to 2 H ‐naphtho[1,2‐ b ]thiete ( 5 ). The benzotriazolyl group proved to be a good leaving group; however, a subsequent nitrogen extrusion takes place under flash vacuum pyrolysis conditions and cyclopentadienecarbonitriles 6a,b are formed by a ring contraction (Scheme 1). Cycloaddition reactions of 5 and dienophiles or heterodienophiles yield the naphtho‐condensed sulfur heterocycles 8, 10, 12 and 14 (Scheme 2).