Application of the 2(5H)furanone motif in the synthesis of new thiopyrano[2, 3-d]thiazoles via the hetero-Diels–Alder reaction and related tandem processes. Issue 30 (27th July 2016)

• Record Type: Journal Article
• Authors: Lozynskyi, Andrii; Zimenkovsky, Borys; Karkhut, Andriy; Polovkovych, Svyatoslav; Gzella, Andrzej K.; Lesyk, Roman
• Is Part Of: Tetrahedron letters. Volume 57:Issue 30(2016)
• Page Start: 3318
• Page End: 3321
• Publication Date: 2016-07-27
• Subjects: Thiopyrano[2, 3-d]thiazoles -- Hetero-Diels–Alder reaction -- Tandem reactions -- 5-Arylidene-4-thioxo-2-thiazolidinones; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.06.060
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 2(5 H )Furanone was used for the synthesis of thiopyrano[2, 3- d ]thiazoles. Acylation–hetero-Diels–Alder reaction was used for the synthesis of chromenothiopyranothiazoles. Regio- and stereoselectivities of the reactions were discussed. Abstract: Novel thiopyrano[2, 3- d ]thiazole derivatives were synthesized from 5-arylidene-4-thioxo-2-thiazolidinones and 2(5 H )furanone in 62–79% yields via hetero-Diels–Alder reactions and related acylation-based tandem processes. The reaction of 5-(4-fluorophenyl)-4-thioxo-2-thiazolidinone with 2(5 H )furanone was studied by DFT at the M06-2X/6-31+G(d, p) level. The stereo- and regioselectivities of cycloaddition were confirmed by NMR spectra and single-crystal X-ray diffraction analyses.