4-Chloro-3-(trifluoroacetyl)coumarin as a novel building block for the synthesis of 7-(trifluoromethyl)-6H-chromeno[4,3-b]quinolin-6-ones

Tetrahedron Letters

Volumn 52, Issue 3, 2011, Pages 373-376

  Iaroshenko, Viktor O ^a,b   Ali, Sajid ^a   Babar, Tariq Mahmood ^a   Dudkin, Sergii ^a   Mkrtchyan, Satenik ^a   Rama, Nasim Hasan ^c   Villinger, Alexander ^a   Langer, Peter ^a,d  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^c QUAID I AZAM UNIVERSITY   (Pakistan)

^d LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Anilines; Chromeno 4,3 b quinolines; Coumarins; Cyclization; Fluorine; Heterocycles

Indexed keywords

4 CHLORO 3 (TRIFLUOROACETYL)COUMARIN; 4 HYDROXYCOUMARIN; 7 (TRIFLUOROMETHYL) 10 METHOXY 6H CHROMENO[4,3 B]QUINOLIN 6 ONE; ANILINE DERIVATIVE; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; PHOSPHORUS DERIVATIVE; PHOSPHORUS OXYCHLORIDE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; RING OPENING;

EID: 78650231841     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.028     Document Type: Article

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58. -1): ν = 3084 (w), 1727 (m), 1605 (w), 1584 (m), 1480 (w), 1453 (m), 1315 (s), 1276 (w), 1237 (w), 1195 (m), 1170 (s), 1156 (s), 1135 (m), 1073 (m), 1034 (w), 974 (m), 851 (m), 820 (m), 766 (s), 723 (s), 657 (m), 625 (w), 606 (w), 582 (m).
59. Procedure for the synthesis of compound 4a. Synthesis was conducted in a pressure tube. To the suspension of 4-hydroxycoumarin (2.5 g, 15.4 mmol) in dry 1,4-dioxane was added 2.56 g (32.4 mmol) of dry pyridine. After a brief stirring, when the mixture became completely homogeneous, were added 2.01 g (18.5 mmol) of trimethylsilylchloride. The reaction mixture was stirred for 1 h at room temperature. Then was added 4.21 g (20.0 mmol) of trifluoroacetic anhydride and the mixture was stirred for another 2 h at 80-90 °C. To the cooled reaction mass was added 2.36 g (15.4 mmol) of phosphorus oxychloride and the mixture was stirred for 2 h at 60 °C. Then the reaction mass was diluted with ice water and extracted with chloroform (50 ml), the chloroform layer was separated, and the water phase was extracted two times with chloroform (50 ml). The combined extract was dried under sodium sulphate, chloroform was removed and the residue was dried in a high vacuum on a boiling water bath. Yield 3.94 g (93%). To obtain product of extra high purity sublimation in vacuum was used. In this case, the yield is 3.29 g (77%).
60. D.L. Chizhov, V.Y. Sosnovskikh, M.V. Pryadeina, Y.V. Burgart, V.I. Saloutin, and V.N. Charushin Synlett 2008 281 285
61. CCDC-794415 for 4a contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk.
62. D.M. Volochnyuk, S.V. Ryabukhin, A.S. Plaskon, and O.O. Grygorenko Synthesis 2009 3719
63. General procedure for the synthesis of compounds 6. Synthesis was carried out in a pressure tube. To a solution of compound 4 (0.3 g, 1.08 mmol) and equimolar amount of aniline in DMF (15 ml) was added TMSCl (1 ml) dropwise. The reaction was heated for 12-24 h at 110-120 °C (controlled by TLC). After cooling the pressure tube, the reaction mixture was poured into water. The precipitate formed was filtered and dried. The product was purified on column chromatography. The products 6 were obtained in good to excellent yield (60-85%).
64. -1): ν = 3084 (w), 1727 (m), 1605 (w), 1584 (m), 1480 (w), 1453 (m), 1315 (s), 1276 (w), 1237 (w), 1195 (m), 1170 (s), 1156 (s), 1135 (m), 1073 (m), 1034 (w), 974 (m), 851 (m), 820 (m), 766 (s), 723 (s), 657 (m), 625 (w), 606 (w), 582 (m).
65. 4 under inert atmosphere. Then reaction mixture was poured into cold water and the formed precipitate was filtered off, washed with diluted sodium carbonate solution, then water and finally dried. The product was purified by column chromatography. The product 7 was obtained in excellent yield (85-95%).
66. 2S (M+H) 362.0457, found 362.0453.
67. CCDC-794413 for 6e contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk.
68. CCDC-794414 for 7i contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk.