N,N-Dimethylpyridin-4-Amine mediated protocol for cyanoethoxycarbonylation of aldehydes under solvent-free conditions

Catalysis Letters

Volumn 137, Issue 3-4, 2010, Pages 255-260

  Khan, Noor Ul H ^a   Agrawal, Santosh ^a   Kureshy, Rukhsana I ^a   Bera, Prasanta K ^a   Abdi, Sayed H R ^a   Bajaj, Hari C ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Aldehydes; Cyanoethoxycarbonylation; Ethylcyanoformate; N,N dimethylpyridin 4 amine; Solvent free

Indexed keywords

ALIPHATIC ALDEHYDES; CYANOETHOXYCARBONYLATION; ENVIRONMENT FRIENDLY; ETHYLCYANOFORMATE; EXPERIMENTAL CONDITIONS; ISOLATED YIELD; N,N-DIMETHYLPYRIDIN-4-AMINE; PRODUCT ISOLATION; ROOM TEMPERATURE; SOLVENT FREE CONDITIONS; SOLVENT-FREE;

SOLVENTS;

ALDEHYDES;

EID: 77956394196     PISSN: 1011372X     EISSN: 1572879X     Source Type: Journal    
DOI: 10.1007/s10562-010-0355-7     Document Type: Article

References (64)

1. Shibasaki M, Kanai M, Funabashi K (2002) J Chem Soc Chem Commun 1989
2. Smith MB, March J (2001) March's advanced organic chemistry, 5th edn. Wiley, New York, p 1239
3. Mori A, Inoue S (1999) In: Jacobsen EN, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric synthesis. Springer-Verlag, Heidelberg, p 983
4. Effenberger F (1994) Angew Chem 106: 1609
5. Effenberger F (1994) Angew Chem Int Ed Engl 33: 1555
6. Kusumoto T, Hanamoto T, Hiyama T, Takehera S, Shoji T, Osawa M, Kuriyama T, Nakamura K, Fujisawa T (1990) Chem Lett 19: 1615
7. Thierry RJA, Lisa AC, Michael N (2005) Synlett 125: 1828
8. Kanai M, Kato N, Ichikawa E, Shibasaki M (2005) Synlett 125: 1491
9. Chen FX, Feng XM (2005) Synlett 125: 892
10. Brunel JM, Holmes IP (2004) Angew Chem Int Ed 43: 2752
11. Michael N (2003) Tetrahedron Asymmetry 14: 147
12. Gregory RJH (1999) Chem Rev 99: 3649
13. Khan NH, Kureshy RI, Abdi SHR, Agrawal S, Jasra RV (2008) Coord Chem Rev 252: 593
14. Xiong Y, Huang X, Gou SH, Huang JL, Wen YH, Feng XM (2006) Adv Synth Catal 348:538
15. Liu XH, Qin B, Zhou X, He B, Feng XM (2005) J Am Chem Soc 127: 12224
16. Ryu HD, Corey EJ (2005) J Am Chem Soc 127: 5384
17. Fuerst DE, Jacobsen EN (2005) J Am Chem Soc 127: 8964
18. Wen YH, Huang X, Hang JL, Xiong Y, Qin B, Feng XM (2005) Synlett 125: 2445
19. Qin YC, Liu L, Pu L (2005) Org Lett 7: 2381
20. Li Y, He B, Qin B, Feng XM, Zhang GL (2004) J Org Chem 69: 7910
21. Tian SK, Hong R, Deng L (2003) J Am Chem Soc 125: 9901
22. Griengl H, Hickel A, Johnson DV, Kratky C, Schmidt M, Schwab H, (1997) J Chem Soc Chem Commun 1933
23. Effenberger F (1999) Chimia 53: 3
24. Schmidt M, Griengl H (1999) Top Curr Chem 200: 193
25. Seoane G (2000) Curr Org Chem 4: 283
26. Chen F, Feng X, Qin B, Zhang G, Jiang Y (2003) Org Lett 5: 949
27. Chen FX, Zhou H, Liu X, Qin B, Feng X, Zhang G, Jiang Y (2004) Chem Eur J 10: 4790
28. Li Q, Liu X, Wang J, Shen K, Feng X (2006) Tetrahedron Lett 47: 4011
29. hen K, Liu X, Li Q, Feng X (2008) Tetrahedron 64: 147
30. Qin B, Liu X, Shi J, Zheng K, Zhao H, Feng X (2007) J Org Chem 72: 2374
31. Kobayashi S, Tsuchiya Y, Mukaiyama, T (1991) Chem Lett 537
32. Prasad AK, Kumar V, Maity J, Wang Z, Ravikumar VT, Sanghvi YS, Parmar VS (2005) Synth Commun 35: 935
33. Hunig S, Schaller R (1982) Angew Chem Int Ed 21: 36
34. Havel M, Velek J, Pospisek J, Soucek M (1979) Collect Czech Chem Commun 44: 2443
35. Abbas SA, Haines AH (1975) Carbohydr Res 39: 358
36. Holy A, Soucek M (1971) Tetrahedron Lett 12: 185
37. Wang W, Gou S, Liu X, Feng X (2007) Synlett 18: 2875
38. Okimoto M, Chiba T (1996) Synthesis 10:1188
39. Yoneda R, Santo K, Harusawa S, Kurihara T (1986) Synthesis 12: 1054
40. Hoffmann HMR, Ismail ZM, Hollweg R, Zein AR (1990) Bull Chem Soc Jpn 63: 1807
41. Zhang W, Shi M (2006) Org Biomol Chem 4: 1671
42. Wang X, Tian SK (2007) Synlett 9: 1416
43. Belokon YN, Blacker AJ, Clutterbuck LA, North M (2003) Org Lett 5: 4505
44. Lundgren S, Wingstrand E, Penhoat M, Moberg C (2005) J Am Chem Soc 127: 11592
45. Chen SK, Peng D, Zhou H, Wang LW, Chen FX, Feng XM (2007) Eur J Org Chem 4: 639
46. Gou S, Wang J, Liu X, Wang W, Chen FX, Feng X (2007) Adv Synth Catal 349: 343
47. Casas J, Baeza A, Sansano JM, Nájera CJ, SaáM (2003) Tetrahedron Asymmetry 14: 197
48. Belokon YN, Clegg WR, Harrington W, Ishibashi E, Nomura H, North M (2007) Tetrahedron 63: 9724
49. Tian J, Yamagiwa N, Matsunaga S, Shibasaki M (2002) Angew Chem Int Ed 41: 3636
50. Yamagiwa N, Tian J, Matsunaga S, Shibasaki M (2005) J Am Chem Soc 127: 3413
51. Poirier D, Berthiaume D, Boivin RP (1999) Synlett 9: 1423
52. Berthiaume D, Poirier D (2000) Tetrahedron 56: 5995
53. Tian SK, Deng L (2001) J Am Chem Soc 123: 6195
54. Tian SK, Deng L (2006) Tetrahedron 62: 11320
55. Watahiki T, Ohba S, Oriyama T (2003) Org Lett 5: 2679
56. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Singh S, Jasra RV (2007) J Organomet Chem 692: 4361
57. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Singh S, Suresh E, Jasra RV (2008) Tetrahedron Lett 49:640
58. Kureshy RI, Agrawal S, Saravanan S, Khan NH, Shah AK, Abdi SHR, Bajaj HC, Suresh E (2010) Tetrahedron Lett 51: 489
59. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Mayani VJ, Jasra RV (2006) Tetrahedron Asymmetry 17: 2659
60. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Mayani VJ, Jasra RV (2007) J Mol Catal 264: 140
61. Khan NH, Agrawal S, Kureshy, RI, Abdi, SHR, Mayani VJ, Jasra RV (2006) Eur J Org Chem 14: 3175
62. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Prathap KJ, Jasra RV (2009) Chirality 21: 262
63. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Prathap KJ, Jasra RV (2008) Eur J Org Chem 26: 4511
64. Khan NH, Agrawal S, Kureshy RI, Abdi SHR, Pathak K, Bajaj HC (2010) Chirality 22: 153