SCOPUS 정보 검색 플랫폼

Volumn , Issue 2, 2008, Pages 281-285

The first synthesis of 4-unsubstituted 3-(trifluoroacetyl)coumarins by the knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by chromene-coumarin recyclization

(6) Chizhov, Dmitrii L a Sosnovskikh, Vyacheslav Ya b Pryadeina, Marina V a Burgart, Yanina V a Saloutin, Victor I a Charushin, Valery N a

a INSTITUTE OF ORGANIC SYNTHESIS (Russian Federation)

b URAL FEDERAL UNIVERSITY (Russian Federation)

Author keywords

3 (trifluoroacetyl)coumarins; Chromene coumarin recyclization; Ethyl trifluoroacetoacetate; Knoevenagel condensation; Salicylaldehydes

Indexed keywords

3 (TRIFLUOROACETYL) COUMARIN DERIVATIVE; ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CHLOROBENZENE; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; ETHYL TRIFLUOROACETATE; PIPERIDINE; SALICYLALDEHYDE; SULFONIC ACID DERIVATIVE; TOLUENE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; KNOEVENAGEL CONDENSATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 38849104865 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000867 Document Type: Article

Times cited : (33)

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- Typical Procedure for Preparation of 6 A mixture of salicylaldehyde (5.0 mmol, ethyl trifluoroacetoacetate (5.0 mmol) and piperidinium acetate (4 mg, 5 mol, was refluxed in MeCN (10 mL) for 3-4 h and then diluted with H2O (30 mL, The precipitate that formed was filtered, washed with warm H2O (50°C, 5 x 10 mL) and dried on air to give 6. Data for Compounds 6a,d Compound 6a: colorless crystals; mp 102-103°C (hexane, IR (mull, ν, 3294, 1686, 1635, 1607, 1576 cm-1. 1H NMR (400 MHz, CDCl3, δ, 1.40 (t, J, 7.2 Hz, 3 H, Me, 4.38 (q, J, 7.2 Hz, 2 H, OCH 2, 7.01-7.06 (m, 2 H, H-6, H-8, 7.26 (dd, J, 7.9, 1.7 Hz, 1 H, H-5, 7.39 (ddd, J, 8.2, 7.5, 1.7 Hz, 1 H, H-7, 7.50 (s, 1 H, OH, 7.78 (s, 1 H, H-4, 19F NMR (376 MHz, CDCl3, δ (C6F6, 74.50 (s, CF3, 13C NMR 100 MHz, CDCl
- 6 (%): C, 46.86; H, 3.03; F, 17.10; N, 4.20. Found: C, 46.73; H, 3.16; F, 16.97; N, 4.29.

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- General Procedure for Preparation of 7 A mixture of chromene 6 (0.5 mmol) and TsOH·H2O (10 mg, 10 mol., was refluxed in chlorobenzene (5 mL) for 10-17 h and then concentrated to ca. 2 mL in The resulting reaction mixture was dried in vacuo, dissolved in toluene (15 mL) and washed with H2O (3 x 5 mL, Toluene solution was refluxed with a Dean-Stark trap for 5 h, the solvent was evaporated in vacuo and the residue was sublimed affording 7. Data for Compounds 7a,d Compound 7a: pale yellow crystals; mp 117-118°C. IR (mull, ν, 1752, 1696, 1605, 1558 cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.38-7.45 (m, 1 H, H-8, H-6, 7.70 (dd, J, 7.8, 1.6 Hz, 1 H, H-5, 7.76 (ddd, J, 8.2, 7.6, 1.6 Hz, 1 H, H-7, 8.52 (s, 1 H, H-4, 19F NMR (376 MHz, CDCl3, δ (C6F 6, 88.37 (s, CF3, 13C NMR 100 MHz, CDCl3
- 5 (%): C, 46.01; H, 1.40; N, 4.88; F, 19.85. Found: C, 46.00; H, 1.15; N, 4.72; F, 19.94.

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