ZrCl4-catalyzed efficient synthesis of enaminones and enamino esters under solvent-free conditions

Monatshefte fur Chemie

Volumn 138, Issue 1, 2007, Pages 77-81

  Lin, Jin ^a   Zhang, Li Feng ^b  

^a HEBEI NORMAL UNIVERSITY   (China)

^b Hebei Chemical and Pharmaceutical Vocational Technology College   (China)

Author keywords

Enamino esters; Enaminones; 1,3 Dicarbonyl compounds; Solvent free conditions; Zirconium(IV) chloride

Indexed keywords

EID: 33845992155     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-006-0565-2     Document Type: Article

References (53)

1. a) Potin D, Dumas F, d'Angelo J (1990) J Am Chem Soc 112: 3483;
2. b) Bartoli G, Cimarelli C, Marcantoni E, Palmieri G, Petrini M (1994) J Org Chem 59: 5328;
3. c) Palmieri G, Cimmerelli C (1996) J Org Chem 61: 5557;
4. d) Beholz LG, Benovsky R, Ward DL, Bata NS, Stille JR (1997) J Org Chem 62: 1033;
5. e) Ferraz HMC, Pereira FLC, Leite FS, Nuns MRS, Payret-Arrua ME (1999) Tetrahedron 55: 10915;
6. f) David O, Blot J, Bellec C, Fargeau-Bellassoued MC, Haviari G, Celerier JP, Lhommet G, Gramain JC, Garadette D (1999) J Org Chem 64: 3122
7. YF Wang T Izawa S Kobayashi M Ohno 1982 J Am Chem Soc 104 6465
8. JP Michael CB Koning GD Hosken TV Stanbury 2001 Tetrahedron 57 9635
9. DL Boger T Ishizaki JRJ Wysocki SA Munk PA Kitos O Suntornwat 1989 J Am Chem Soc 111 6461
10. a) Baraldi PG, Simoni D, Manfredini S (1983) Synthesis 902;
11. b) Cone EJ, Garner RH, Hayes AW (1972) J Org Chem 26: 4436
12. a) Hannick SM, Kishi Y (1983) J Org Chem 48: 3833;
13. b) Lee AS-Y, Cheng R-Y (1997) Tetrahedron Lett 38: 443;
14. c) Bird TGC, Olivier A (1996) Bioorg Med Chem Lett 6: 515
15. a) Fukuyama T, Yung YM (1981) Tetrahedron Lett 22: 3759;
16. b) Jiang N, Qu Z, Wang J (2001) Org Lett 3: 2989
17. S Fustero B Pina A Simón Fuentes 1997 Tetrahedron Lett 38 6771
18. a) Bartoli G, Cimarelli C, Dalpozzo R, Palmieri G (1995) Tetrahedron 51: 8613;
19. b) Katritzky AR, Fang Y, Donkor A, Xu J (2000) Synthesis 2029
20. G Cimarelli G Palmieri E Volpini 2004 Tetrahedron Lett 45 6629
21. a) Saeed AAH (1984) J Chem Eng Data 29: 358;
22. b) Hauser CR, Reynolds GA (1948) J Am Chem Soc 70: 2402;
23. c) Martin DF, Janusonis GA, Martin BB (1961) J Am Chem Soc 83: 73;
24. d) Yapi AD, Mustofa M, Valentin A, Chavignon O, Teulade J-C, Mallie M, Chapat J-P, Blache Y (2000) Chem Pharm Bull 48: 1886;
25. e) Brandt CA, Da Silva ACMP, Pancote CG, Brito CL, Da Silveira MAB (2004) Synthesis 1557
26. a) Bartoli G, Bosco M, Locatelli M, Marcantoni E, Melchiorre P, Sambri L (2004) Synlett 239;
27. b) Khodaei MM, Khosropour AR, Kookhazadeh M (2004) Synlett 1980;
28. c) Arcadi A, Bianchi G, Di Giuseppe S, Marinelli F (2003) Green Chem 5: 64;
29. d) Khosropour AR, Khodaei MM, Kookhazadeh M (2004) Tetrahedron Lett 45: 1725;
30. e) Vohra RK, Renaud J-L, Bruneau C (2005) Collect Czech Chem Commun 70: 1943;
31. f) Zhang Z-H, Yin L, Wang Y-M (2006) Adv Synth Catal 348: 184;
32. g) Zhang Z-H, Hu J-T (2006) J Braz Chem Soc 17: 1497;
33. h) Zhang Z-H, Ma Z-C, Mo L-P (2006) Indian J Chem 45B: (in press)
34. S Gogoi R Bhuyan NC Barua 2005 Synth Commun 35 2811
35. a) Braibante MEF, Braibantre GB, Rosso DA, Oriques DA (2003) J Braz Chem Soc 14: 994;
36. b) Braibante MEF, Braibante HTS, Morel AF, Costa CC, Lima MG (2006) J Braz Chem Soc 17: 184
37. Y-H Gao Q-H Zhang J-X Xu 2004 Synth Commun 34 909
38. Zhang Z-H, Song L-M (2005) J Chem Res 817
39. Bhosale RS, Suryawanshi PA, Ingle SA, Lokhande MN, More SP, Mane SB, Bhosale SV, Pawar RP (2006) Synlett 933
40. B Das K Venkateswarlu A Majhi MR Reddy KN Reddy YK Rao K Ravikumar B Sridhar 2006 J Mol Catal A Chem 246 276
41. AR Gholap NS Chakor T Daniel RJ Lahoti KV Srinivasa 2006 J Mol Catal A Chem 245 37
42. K Tanaka F Toda 2000 Chem Rev 100 1025
43. a) Zhang Z-H, Yin L, Wang Y-M (2005) Synthesis 1949;
44. b) Sharma GVM, Srinivas B, Krishna PR (2005) Lett Org Chem 2: 57;
45. c) Zhang Y, Shibatomi K, Yamamoto H (2005) Synlett 2837;
46. d) Bora U, Saikia A, Boruah RC (2005) Indian J Chem 44B: 2523;
47. e) Sharma GVM, Reddy JJ, Lakshmi PS, Krishna PR (2005) Tetrahedron Lett 46: 6119;
48. f) Firouzabadi H, Iranpoor N, Jafarpour M (2005) Tetrahedron Lett 46: 4107;
49. g) Smitha G, Patnaik S, Reddy CS (2005) Synthesis 711;
50. h) Yadav JS, Rajasekhar K, Murty MSR (2005) Tetrahedron Lett 46: 2311;
51. i) Meshram HM, Lakshindra C, Reddy PN, Sadashiv K, Yadav JS (2006) Synth Commun 36: 795;
52. j) Firouzabadi H, Iranpoor N, Jafarpour M (2006) Tetrahedron Lett 47: 93;
53. k) Yadav JS, Rajasekhar K, Murty MSR (2006) Tetrahedron Lett 47: 6149