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- Title
Synthesis of Functionalized Arenopyrans and Arenylsulfanes by Reacting Nitroallylic Acetates with Arenols and Arenethiols.
- Authors
Basu, Pallabita; Sikdar, Robi; Kumar, Tarun; Namboothiri, Irishi N. N.
- Abstract
Nitroallylic acetates react with naphthols and electron‐rich phenols under mild conditions (TEA, DCM, room temp.) to afford arenopyrans in moderate to excellent yields. Such (3+3) annulation of a 1,3‐bielectrophilic nitroallylic acetate and a 1,3‐binucleophilic arenol involving an SN2′ reaction and an intramolecular 6‐endo‐trig cyclization takes place in a regio‐ and stereoselective manner. Surprisingly, the reaction of arenethiols under the same conditions provided nitroallylic thioethers instead of the expected arenothiopyrans presumably through a direct SN2 reaction. (3+3) Annulation of a 1,3‐bielectrophilic nitroallylic acetate and a 1,3‐binucleophilic arenol involving an SN2′ reaction and an intramolecular 6‐endo‐trig cyclization takes place in a regio‐ and stereoselective manner to provide arenopyrans. Interestingly, the reaction of arenethiols under the same conditions provided nitroallylic thioethers through a direct SN2 reaction.
- Subjects
ORGANIC cyclic compounds; NAPHTHOL derivatives; PHENOL; RING formation (Chemistry); CRYSTAL structure
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 41, p5735
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201801132