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An alternative route to 2H-naphtho[1,2-b]thiete and its cycloaddition products

✍ Scribed by Norbert Rumpf; Dieter Gröschl; Herbert Meier; Daniela C. Oniciu; Alan R. Katritzky

Book ID: 102340356
Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 242 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350648

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✦ Synopsis

Abstract

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).

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