Three-component coupling of isoquinoline, activated alkyne and nitromethane: A facile synthesis of nitromethyl derivatives of 1,2-dihydroisoquinolines

Synthesis

Volumn , Issue 7, 2009, Pages 1131-1136

  Yadav, Jhillu S ^a   Subba Reddy, Basi V ^a   Yadav, Nagendra Nath ^a   Gupta, Manoj K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Activated alkynes; Aza Henry reaction; Isoquinoline quinoline; Nitromethane

Indexed keywords

ACTIVATED ALKYNES; AZA-HENRY REACTION; DIHYDROISOQUINOLINES; FACILE SYNTHESIS; HIGH SELECTIVITY; ISOQUINOLINE; ISOQUINOLINE/QUINOLINE; NITROMETHANE; THREE-COMPONENT COUPLING;

ACETYLENE;

3 [1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL] 1 PHENYLPROP 2 EN 1 ONE; ALKYNE DERIVATIVE; DIETHYL 2 [1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]MALEATE; DIMETHYL 2 [1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]MALEATE; ETHYL 3 [1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; ETHYL 3 [3 METHYL 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; ETHYL 3 [4 BROMO 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; ETHYL 3 [5 BROMO 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; ISOCARBOSTYRIL DERIVATIVE; ISOQUINOLINE; METHYL 3 [1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; METHYL 3 [2 (NITROMETHYL)QUINOLIN 1(2H) YL]ACRYLATE; METHYL 3 [3 METHYL 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; METHYL 3 [4 BROMO 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; METHYL 3 [5 BROMO 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; METHYL 3 [5 NITRO 1 (NITROMETHYL)ISOQUINOLIN 2(1H) YL]ACRYLATE; NITROMETHANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROOM TEMPERATURE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 67650045600     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1088004     Document Type: Article

References (38)

1. (a) Ramon, D. J.; Yus, M. Angew. Chem. Int. Ed. 2005, 44, 1602.
2. (b) Nair, V.; Rajesh, C.; Vinod, A. U.; Bindu, S.; Sreekenth, A. R.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
3. (c) Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471.
4. (d) Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 4101.
5. (e) Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
6. (f) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 3321.
7. (g) Weber, L.; Illgen, K.; Almstetter, M. Synlett 1999, 366.
8. (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
9. (b) Chan, C.; Heid, R.; Zheng, S.; Guo, J.; Zhou, B.; Furuuchi, T.; Danishefsky, S. J. J. Am. Chem. Soc. 2005, 127, 4596.
10. (c) Vincent, G.; Williams, R. M.; Gan, E. F.; Williams, R. M. Angew. Chem. Int. Ed. 2007, 46, 1517.
11. (a) Gensler, W. J.; Lawless, S. F.; Bluhm, A. L.; Dertouzos, H. J. Org. Chem. 1975, 40, 733.
12. (b) Beugelmans, R.; Chastanet, J.; Roussi, G. Tetrahedron 1984, 40, 311.
13. (c) Magnus, P.; Matthew, K. S.; Lynch, V. Org. Lett. 2003, 5, 2181.
14. (d) Kadzimirsz, D.; Hildebrandt, D.; Merz, K.; Dyker, G. Chem. Commun. 2006, 661.
15. (a) Miller, R. B. Tetrahedron Lett. 1998, 39, 1721.
16. (b) Lorsbach, B. A.; Bagdanoff, J. T.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1998, 63, 2244.
17. (c) Lee, S. H.; Park, Y. S.; Nam, M. H.; Yoon, C. M. Org. Biomol. Chem. 2004, 2, 2170.
18. (d) Taylor, S. J.; Taylor, A. M.; Schreiber, S. L. Angew. Chem. Int. Ed. 2004, 43, 1681.
19. (e) Diaz, J. L.; Miguel, M.; Lavilla, R. J. Org. Chem. 2004, 69, 3550.
20. (f) Ullah, E.; Rotzoll, S.; Schmidt, A.; Michalik, D.; Langer, P. Tetrahedron Lett. 2005, 46, 8997.
21. (g) Hewavitharanage, P.; Danilov, E. O.; Neckers, D. C. J. Org. Chem. 2005, 70, 10653.
22. (a) Takamura, M.; Funbashi, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6327.
23. (b) Funabashi, K.; Ratni, H.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 10784.
24. (c) Alexakis, A.; Amiot, F. Tetrahedron: Asymmetry 2002, 13, 2117.
25. (d) Taylor, M. S.; Tokunaga, N.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2005, 44, 6700.
26. (e) Taylor, A. M.; Schreiber, S. L. Org. Lett. 2006, 8, 143.
27. (f) Lu, S.; Wang, Y.; Han, X.; Zhau, Y. Angew. Chem. Int. Ed. 2006, 45, 2260.
28. (a) Yadav, J. S.; Reddy, B. V. S.; Gupta, M. K.; Prabhakar, A.; Jagadeesh, B. Chem. Commun. 2004, 2124.
29. (b) Yadav, J. S.; Reddy, B. V. S.; Srinivas, M.; Sathaiah, K. Tetrahedron Lett. 2005, 46, 3489.
30. (c) Yadav, J. S.; Reddy, B. V. S.; Srinivas, M.; Sathaiah, K. Tetrahedron Lett. 2005, 46, 8905.
31. (d) Yadav, J. S.; Reddy, B. V. S.; Gupta, M. K.; Prahap, I.; Dash, U. Synthesis 2007, 1077.
32. (e) Yadav, J. S.; Reddy, B. V. S.; Gupta, M. K.; Dash, U.; Bhunia, D. C.; Hossain, S. S. Synlett 2007, 2801.
33. (a) Yadav, J. S.; Reddy, B. V. S.; Yadav, N. N.; Gupta, M. K.; Sridhar, B. J. Org. Chem. 2008, 73, 6857.
34. (b) Yadav, J. S.; Reddy, B. V. S.; Yadav, N. N.; Gupta, M. K. Tetrahedron Lett. 2008, 49, 2815.
35. (a) Winterfeldt, E. Angew. Chem. Int. Ed. Engl. 1967, 6, 424.
36. (b) Johnson, A. W.; Tebby, J. C. J. Chem. Soc. 1961, 2126.
37. (c) Tebby, J. C.; Wilson, I. F.; Griffiths, D. V. J. Chem. Soc., Perkin Trans. 1 1979, 2133.
38. (d) Butterfield, P. J.; Tebby, J. C.; Griffiths, D. V. J. Chem. Soc., Perkin Trans. 1 1979, 1189.