Synthesis of chalcones and flavanones using Julia–Kocienski olefination

• Published in: Tetrahedron Vol. 66; no. 48; pp. 9445 - 9449
• Main Authors: Kumar, Atul, Sharma, Siddharth, Tripathi, Vishwa Deepak, Srivastava, Suman
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 27.11.2010; Elsevier
• Subjects: Aldehydes; Chalcone; Chemistry; Chemistry, Organic; Exact sciences and technology; Flavanones; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Julia–Kocienski olefination; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Synthesis (chemistry); Tetrahedrons; Flavanones; Julia–Kocienski olefination; OSDKDQSRACTQQE-UHFFFAOYSA-N; Chalcone; Julia-Kocienski olefination; STEREOCHEMISTRY; TRANSFER HYDROGENATION; CARBONYL-COMPOUNDS; CARBANIONS; STEREOSELECTIVE-SYNTHESIS; INHIBITORS; ALPHA,BETA-UNSATURATED ESTERS; 3,5-BIS(TRIFLUOROMETHYL)PHENYL SULFONES; DERIVATIVES; HIGH-YIELD SYNTHESIS; One pot reaction; Sulfur nitrogen heterocycle; Chemical reagent; Aldehyde; Benzothiazole derivatives; Oxygen heterocycle; Flavonoid; Flavanone derivatives; Cyclization; Aromatic compound; Chemical synthesis; Julia olefination
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2010.09.089

A new application of Julia–Kocienski olefination for the synthesis of chalcones and flavanones has been described. 2-(Benzo[ d]thiazol-2-ylsulfonyl)-1-phenylethanones have been developed as new reagents for direct Julia–Kocienski olefination with aldehydes in the presence of a base, afforded chalcones in good to excellent yields. Whereas, 2-(benzo[ d]thiazol-2-ylsulfonyl)-1-(2-hydroxyphenyl)ethanone reacted with the aromatic aldehydes to furnish flavanones in good yields via one-pot intra-molecular cyclization. [Display omitted]