Regioselective carbon-carbon bond formation in the reaction of 2-hydroxy-2-(trifluoromethyl)-2H-chromenes with indoles promoted by Lewis acid

Synthesis

Volumn , Issue 20, 2011, Pages 3364-3370

  Pang, Wan ^a,b   Han, Jian Wei ^b   Zhao, Jing Wei ^b   Zhu, Shi Zheng ^b  

^a SHANGHAI INSTITUTE OF TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2 H chromenes; C C bond formation; indoles; Lewis acid; regioselective

Indexed keywords

C-C BOND FORMATION; CHROMENES; INDOLES; LEWIS ACID; REGIO-SELECTIVE;

REGIOSELECTIVITY;

2 HYDROXY 2(TRIFLUOROMETHYL) 2H CHROMENE DERIVATIVE; CARBON; CHROMENE DERIVATIVE; ETHYL 2 (1 ALLYL 1H INDOL 3 YL) 2 (TRIFLUOROMETHYL) 2H CHROMENE 3 CARBOXYLIC ACID; ETHYL 2 (1 ISOPROPYL INDOL 3 YL) 2 (TRIFLUOROMETHYL) 2H CHROMENE 3 CARBOXYLIC ACID; ETHYL 2 (1 METHYL 1H INDOL 3 YL) 2 (TRIFLUOROMETHYL) 2H CHROMENE 3 CARBOXYLIC ACID; ETHYL 3 [3 (ETHOXYCARBONYL) 2 (TRIFLUOROMETHYL) 4H CHROMENE 4 YL] 1H INDOLE 1 CARBOXYLIC ACID; ETHYL 3 [6 CHLORO 3 (ETHOXYCARBONYL) 2 (TRIFLUOROMETHYL) 4H CHROMENE 4 YL] 1H INDOLE 1 CARBOXYLIC ACID; ETHYL 4 (1 ACETYL 1H INDOL 3 YL) 2 (TRIFLUOROMETHYL) 4H CHROMENE 3 CARBOXYLIC ACID; ETHYL 4 (1 ACETYL 1H INDOL 3 YL) 6 BROMO 2 (TRIFLUOROMETHYL) 4H CHROMENE 3 CARBOXYLIC ACID; ETHYL 6 CHLORO 2 (1 METHYL 1H INDOL 3 YL) 2 (TRIFLUOROMETHYL) 2H CHROMENE 3 CARBOXYLIC ACID; INDOLE DERIVATIVE; LEWIS ACID; NUCLEOPHILE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; FLUORINE NUCLEAR MAGNETIC RESONANCE; MASS SPECTROMETRY; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 80053911053     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1260202     Document Type: Article

References (43)

1. Shirakawa S, Kobayashi S, Org. Lett. 2007 9 311
2. Piao C R., Zhao Y L., Han X D., Liu Q, J. Org. Chem. 2008 73 2264; and references cited therein
3. Yasuda M, Somyo T, Baba A, Angew. Chem. Int. Ed. 2006 45 793
4. OConnor P D., Marino M G., Guéret S M., Brimble M A., J. Org. Chem. 2009 74 8893
5. VenkateswaraRao K T., Rao P S. N., SaiPrasad P S., Lingaiah N, Catal. Commun. 2009 10 1394
6. Kaur G, Kausik M, Trehan S, Tetrahedron Lett. 1997 38 2521
7. Xiang S K., Zhang L H., Jiao N, Chem. Commun. 2009 42 6487
8. Mirza-Aghayan M, Boukherroub R, Rahimifard M, Tetrahedron Lett. 2009 50 5930
9. Bunge A, Hamann H J., McCalmont E, Liebscher J, Tetrahedron Lett. 2009 50 4629
10. Shi F, Tse M K., Cui X J., Gördes D, Michalik D, Thurow K, Deng Y Q., Beller M, Angew. Chem. Int. Ed. 2009 48 5912
11. Ahmad R, Riahi A, Langer P, Tetrahedron Lett. 2009 50 1490
12. Kharrat S E., Laurent P, Blancou H, J. Org. Chem. 2006 71 8637; and references cited therein
13. Bera K, Sarkar S, Biswas S, Maiti S, Jana U, J. Org. Chem. 2011 76 3539
14. Engler T A., LaTessa K O., Iyengar R, Chai W, Agrios K, Bioorg. Med. Chem. 1996 4 1755
15. Kashiwada Y, Yamazaki K, Ikeshiro Y, Yamagishi T, Fujioka T, Mihashi K, Mizuki K, Cosentino L M., Fowke K, Morris-Natschke S L., Lee K H., Tetrahedron 2001 57 1559
16. Elomri A, Mitaku S, Michel S, Skaltsounis A L., Tillequin F, Koch M, Pierre A, Guilbaud N, Léonce S, Kraus-Berthier L, Rolland Y, Atassi G, J. Med. Chem. 1996 39 4762
17. Kidwai M, Saxena S, Khan M K. R., Thukral S S., Bioorg. Med. Chem. Lett. 2005 15 4295
18. Tahtaoui C, Demailly A, Guidemann C, Joyeux C, Schneider P, [nl] J. Org. Chem. 2010 75 3781
19. Lago J H. G., Ramos C S., Casanova D C. C., Morandim A A., Bergamo D C. B., Cavalheiro A J., Bolzani V S., Furlan M, Guilharães E F., Young M C. M., Kato M J., J. Nat. Prod. 2004 67 1783
20. Bernard C B., Krishnamurty H G., Chauret D, Durst T, Philogene B J. R., SanchezVindas P, Hasbun C, Poveda L, SanRoman L, Arnason J T., J. Chem. Ecol. 1995 21 801
21. Mukai K, Okabe K, Hosose H, J. Org. Chem. 1989 54 557
22. Jankun J, Selman S H., Swiercz R, Nature 1997 387 561
23. Paramonov S, Delbaere S, Fedorova O, Fedorov Y, Lokshin V, Samat A, Vermeersch G, J. Photochem. Photobiol., A 2010 209 111
24. Evans R A., Such G K., Aust. J. Chem. 2005 58 825
25. Zhong W H., Zhao Y Z., Su W K., Tetrahedron 2008 64 5491
26. Bonacorso H G., Navarini J, Wiethan C W., Bortolotto G P., Paim G R., Cavinatto S, Martins M A. P., Zanatta N, Caro M S. B., J. Fluorine Chem. 2011 132 160
27. Brimble M A., Gibson J S., Sperry J, In Comprehensive Heterocyclic Chemistry III Vol. 7 Katritzky A R. Ramsden C A. Scriven E F. V. Taylor R J. K. Elsevier Oxford 2008 419-699
28. Bello D, Ruiz-Rodríguez J, Albericio F, Ramón R, Lavilla R, Eur. J. Org. Chem. 2010 5373
29. Shanthi G, Perumal P T., Tetrahedron Lett. 2007 48 6785
30. Chambers R D., Fluorine in Organic Chemistr y CRC Press Boca Raton (FL, USA) 2004
31. Filler R, Organic Chemistry in Medicinal Chemistry and Biomedical Applications Elsevier Amsterdam 1993
32. Uneyama K, Organofluorine Chemistry Blackwell Publishing Ltd. Malden (MA, USA) 2006
33. Hiyama T, Organofluorine Compounds. Chemistry and Application Springer Berlin 2000
34. Zeng M, You S L., Syntett 2010 1289
35. Cai Q, Zheng C, You S L., Angew. Chem. Int. Ed. 2010 49 8666
36. Kang Q, Zhao Z A., You S L., Tetrahedron 2009 65 1603
37. He Q L., Sun F L., Zheng X J., You S L., Synlett 2009 1111
38. Liu W B., He H, Dai L X., You S L., Synthesis 2009 2076
39. Kang Q, Zheng X J., You S L., Chem. Eur. J. 2008 14 3539
40. Zeng M, Kang Q, He Q L., You S L., Adv. Synth. Catal. 2008 350 2169
41. Kang Q, Zhao Z A., You S L., J. Am. Chem. Soc. 2007 129 1484
42. Wang S Y., Ji S J., Synlett 2007 2222
43. Wang S Y., Ji S J., Synth. Commun. 2008 38 465