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RESEARCH PRODUCT
An alternative route to 2H-naphtho[1,2-b]thiete and its cycloaddition products
Norbert RumpfDaniela Carmen OniciuHerbert MeierAlan R. KatritzkyDieter Gröschlsubject
chemistry.chemical_classificationchemistryFlash vacuum pyrolysisOrganic ChemistryThiolLeaving groupchemistry.chemical_elementSulfurMedicinal chemistryNitrogenCycloadditiondescription
2-(1H-Benzotriazol-1-ylmethyl)-1-naphthalenol (1) can be transformed in high yields to the corresponding thiol 4. Flash vacuum pyrolysis of 4 leads to 2H-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).
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1998-11-01 | Journal of Heterocyclic Chemistry |