Three-component reaction of 2-alkynylbenzaldehyde, amine, and nucleophile using Lewis acid-surfactant combined catalyst in water

Tetrahedron

Volumn 64, Issue 7, 2008, Pages 1378-1382

  Ye, Yang ^a   Ding, Qiuping ^a,c   Wu, Jie ^a,b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^c JIANGXI NORMAL UNIVERSITY   (China)

Author keywords

1,2 Dihydroisoquinoline; Lewis acid surfactant combined catalyst; Ultrasonic; Water

Indexed keywords

1 (HEX 1 YNYL) 2 (4 METHOXYPHENYL) 3 PHENYL 1,2 DIHYDROISOQUINOLINE; 1 (HEX 1 YNYL) 2,3 DIPHENYL 1,2 DIHYDROISOQUINOLINE; 1 [2 (4 PENTYLPHENYL)ETHYNYL] 2,3 DIPHENYL 1,2 DIHYDROISOQUINOLINE; 2 (3 NITROPHENYL) 3 PHENYL 1 (2 PHENYLETHYNYL) 1,2 DIHYDROISOQUINOLINE; 2 (4 CHLOROPHENYL) 3 PHENYL 1 (2 PHENYLETHYNYL) 1,2 DIHYDROISOQUINOLINE; 2 (4 FLUOROPHENYL) 3 PHENYL 1 (3 PHENYLETHYNYL) 1,2 DIHYDROISOQUINOLINE; 2 (4 METHOXYPHENYL) 3 PHENYL 1 (2 PHENYLETHYNYL) 1,2 DIHYDROISOQUINOLINE; 2,3 DIPHENYL 1 (2 PHENYLETHYNYL) 1,2 DIHYDROISOQUINOLINE; 2,3 DIPHENYL 1 [2 (4 TOLYL)ETHYNYL] 1,2 DIHYDROISOQUINOLINE; 3 PHENYL 1 (2 PHENYLETHYNYL) 2 (4 TOLYL) 1,2 DIHYDROISOQUINOLINE; ALKYNE DERIVATIVE; AMINE; ANILINE DERIVATIVE; BENZALDEHYDE DERIVATIVE; ISOQUINOLINE DERIVATIVE; LEWIS ACID; NITROMETHANE; PHENYLACETYLENE; PHOSPHATE; SURFACTANT; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL;

EID: 37649023133     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.11.055     Document Type: Article

References (34)

1. In: Yamamoto H. (Ed). Lewis Acids in Organic Synthesis (2000), Wiley-VCH, Weinheim
2. Otto S., Engberts J.B.F.N., and Kwak J.C.T. J. Am. Chem. Soc. 120 (1998) 9517
3. Manabe K., and Kobayashi S. Chem. Commun. (2000) 669
4. Mori Y., Kakumoto K., Manabe K., and Kobayashi S. Tetrahedron Lett. 41 (2000) 3107
5. Manabe K., Aoyama N., and Kobayashi S. Adv. Synth. Catal. 343 (2001) 174
6. Kobayashi S., and Manabe K. Acc. Chem. Res. 35 (2002) 209
7. Schreiber S.L. Science 287 (2000) 1964
8. Schreiber S.L. Chem. Eng. News 81 (2003) 51
9. For selected examples, see:
10. Zhang L., Meng T., Fan R., and Wu J. J. Org. Chem. 72 (2007) 7279
11. Ding Q., Ye Y., Fan R., and Wu J. J. Org. Chem. 72 (2007) 5439
12. Wang Z., Fan R., and Wu J. Adv. Synth. Catal. 349 (2007) 1943
13. Sun W., Ding Q., Sun X., Fan R., and Wu J. J. Comb. Chem. 9 (2007) 690
14. Wang Z., Wang B., and Wu J. J. Comb. Chem. 9 (2007) 811
15. Bentley K.W. The Isoquinoline Alkaloids Vol 1 (1998), Harwood Academic, Amsterdam
16. Obika S., Kono H., Yasui Y., Yanada R., and Takemoto Y. J. Org. Chem. 72 (2007) 4462 and references cited therein
17. Asao N., Yudha S.S., Nogami T., and Yamamoto Y. Angew. Chem., Int. Ed. 44 (2005) 5526
18. Yanada R., Obika S., Kono H., and Takemoto Y. Angew. Chem., Int. Ed. 45 (2006) 3822
19. Asao N., Iso K., and Yudha S.S. Org. Lett. 8 (2006) 4149
20. Mori S., Uerdingen M., Krause N., and Morokuma K. Angew. Chem., Int. Ed. 44 (2005) 4715
21. Asao N., Chan C.S., Takahashi K., and Yamamoto Y. Tetrahedron 61 (2005) 11322
22. Ohtaka M., Nakamura H., and Yamamoto Y. Tetrahedron Lett. 45 (2004) 7339
23. Witulski B., Alayrac C., and Tevzadze-Saeftel L. Angew. Chem., Int. Ed. 42 (2003) 4257
24. Yavari I., Ghazanfarpour-Darjani M., Sabbaghan M., and Hossaini Z. Tetrahedron Lett. 48 (2007) 3749
25. Shaabani A., Soleimani E., and Khavasi H.R. Tetrahedron Lett. 48 (2007) 4743
26. Wang G.-W., and Li J.-X. Org. Biomol. Chem. 4 (2006) 4063
27. Diaz J.L., Miguel M., and Lavilla R. J. Org. Chem. 69 (2004) 3550
28. Huang Q., and Larock R.C. J. Org. Chem. 68 (2003) 980
29. Dai G., and Larock R.C. J. Org. Chem. 68 (2003) 920
30. Dai G., and Larock R.C. J. Org. Chem. 67 (2002) 7042
31. Huang Q., Hunter J.A., and Larock R.C. J. Org. Chem. 67 (2002) 3437
32. Roesch K.R., and Larock R.C. J. Org. Chem. 67 (2002) 86
33. Roesch K.R., Zhang H., and Larock R.C. J. Org. Chem. 66 (2001) 8042
34. Roesch K.R., and Larock R.C. Org. Lett. 1 (1999) 553