First InCl3-catalyzed, three-component coupling of aldehydes, -naphthol, and 6-amino-1,3-dimethyluracil to functionalized naphthopyranopyrimidines

Synlett

Volumn , Issue 7, 2010, Pages 1133-1137

  Nandi, Ganesh Chandra ^a   Samai, Subhasis ^a   Singh, M S ^a  

^a BANARAS HINDU UNIVERSITY   (India)

Author keywords

InCl3; Multicomponent reaction; Naphthopyranopyrimidine; One pot synthesis

Indexed keywords

2 NAPHTHOL; ALDEHYDE DERIVATIVE; AMMONIA; INDIUM CHLORIDE; NAPHTHOL DERIVATIVE; PYRAN DERIVATIVE; PYRIMIDINE DERIVATIVE; URACIL DERIVATIVE; WATER;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ONE POT SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS;

EID: 77951106045     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219574     Document Type: Article

References (59)

1. Ugi I, Pure Appl. Chem. 2001 73 187; and references therein
2. Devi I, Bhuyan P J., Tetrahedron Lett. 2004 45 8625
3. For a monograph, see: Multicomponent Reactions Zhu J Bienayme H Wiley-VCH Weinheim 2005
4. Dmling A, Chem. Rev. 2006 106 17
5. DSouza D M., Mueller T J. J., Chem. Soc. Rev. 2007 36 3169
6. Cariou C C. A., Clarkson G J., Shipman M, J. Org. Chem. 2008 73 9762
7. Alizadeh A, Mobahedi F, Esmaili A, Tetrahedron Lett. 2006 47 4469
8. Umkeherer M, Kalinski C, Kolb J, Burdack C, Tetrahedron Lett. 2006 47 2391
9. Dmling A, Ugi I, Angew. Chem. Int. Ed. 2000 39 3168
10. Ramon D J., Yus M, Angew. Chem. Int. Ed. 2005 44 1602
11. Tejedor D, Garcia-Tellado F, Chem. Soc. Rev. 2007 36 484
12. Orru R V. A., deGreef M, Synthesis 2003 1471
13. Zhu J P., Eur. J. Org. Chem. 2003 1133
14. Ghahremanzadeh R, Ahadi S, Bazgir A, Tetrahedron Lett. 2009 50 7379
15. Radi M, Schenone S, Botta M, Org. Biomol. Chem. 2009 7 2841
16. Kuo Sh Ch, Huang L J., Nakamura H, J. Med. Chem. 1984 27 539; and references therein
17. Wrigglesworth R, Inglis W D., Livingstone D B., Snekling C J., Wood H C. S., J. Chem. Soc., Perkin Trans. 1 1984 959
18. OCallaghan C N., Conalty M L., Proc. R. Ir. Acad., Sect. B 1983 83 241
19. Bedair A H., El-Hady N A., El-Latif M S. A., Fakery A H., El-Agrody A M., Farmaco 2000 55 708
20. Joshi K C., Jain R, Sharma K, J. Indian Chem. Soc. 1988 45 202
21. El-Agrody A M., AbdEl-Latif M S., El-Hady N A., Fakery A H., Bedair A H., Molecules 2001 6 519
22. Ahluwalia V K., Chopra M, Chandra R, J. Chem. Res., Synop. 2000 162
23. Ahluwalia V K., Chopra M, Chandra R, J. Chem. Res., Miniprint 2000 570
24. Bedair A H., Emam H A., El-Hady N A., Ahmed K A. R., El-Agrody A M., Farmaco 2001 56 965
25. Marugan J, Liu K, Zheng W, Eskay R, Southall N, Heilig M, Inglese J, Austin C, Probe report, MLPCN-Grant X01-DA026210-01
26. Reviews for indium Lewis acids:, Frost C G., Chauhan K K., J. Chem. Soc., Perkin Trans. 1 2000 3015
27. Fringuelli F, Piermatti O, Pizzo F, Vaccaro L, Curr. Org. Chem. 2003 7 1661
28. Frost C G., Hartley J P., Mini-Rev. Org. Chem. 2004 1 1
29. Zhang Z.-H, Synlett 2005 711
30. Zhang Y, Li P, Wang M, Wang L, J. Org. Chem. 2009 74 4364
31. Li C.-J, Chan T.-H, Tetrahedron 1999 55 11149
32. Sharma S D., Hazarika P, Konwar D, Tetrahedron Lett. 2008 49 2216
33. Thirumurugan P, Perumal P T., Tetrahedron 2009 65 7620
34. Shanthi G, Perumal P T., Tetrahedron Lett. 2009 50 3959
35. Loh T.-P, Pei J, Cao G Q., Chem. Commun. 1996 1819
36. Loh T.-P, Wei L.-L, Tetrahedron Lett. 1998 39 323
37. Li Z, Zhang J, Li C J., Tetrahedron Lett. 2003 44 153
38. Zhang J, Li C J., J. Org. Chem. 2002 67 3969
39. Babu G, Perumal P T., Tetrahedron Lett. 1997 38 5025
40. Babu G, Perumal P T., Tetrahedron Lett. 1998 39 3225
41. Teo Y.-C, Loh T.-P, Org. Lett. 2005 7 2539
42. Elamparuthi E, Anniyappan M, Muralidharan D, Perumal P T., ARKIVOC 2005 (xi) 6
43. Loh T.-P, Wei L.-L, Synlett 1998 975
44. Miyai T, Onishi Y, Baba A, Tetrahedron Lett. 1998 39 6291
45. Ranu B C., Eur. J. Org. Chem. 2000 2347
46. Nandi G C., Samai S, Kumar R, Singh M S., Tetrahedron 2009 65 7129
47. Nandi G C., Samai S, Kumar R, Singh M S., Tetrahedron Lett. 2009 50 7220
48. Samai S, Nandi G C., Kumar R, Singh M S., Tetrahedron Lett. 2009 50 7096
49. Samai S, Nandi G C., Kumar R, Singh M S., Tetrahedron 2009 34 10055
50. Kumar R, Nandi G C., Verma R K., Singh M S., Tetrahedron Lett. 2010 51 442
51. Wolff A, Boechmer V, Vogt W, Ugozzoli F, Andreetti G D., J. Org. Chem. 1990 55 5665
52. No K W., Kim J E., Kwon K M., Tetrahedron Lett. 1995 36 8453
53. Mashraqui S H., Patil M B., Mistry H D., Ghadigaonkar S, Meetsma A, Chem. Lett. 2004 1058
54. VandeWater R W., Pettus T R. R., Tetrahedron 2002 58 5367
55. Desimoni G, Tacconi G, Chem. Rev. 1975 75 651
56. Wan P, Backer B, Diao L, Fischer M, Shi Y, Yang C, Can. J. Chem. 1996 74 465
57. Turner A B., Q. Rev. Chem. Soc. 1964 18 347
58. Schleigh W R., Org. Chem. Bull. 1971 43 1
59. Bloch R, Chem. Rev. 1998 98 1407