Reduction of carboxylic acids using esters of benzotriazole as high-reactivity intermediates

Synthesis

Volumn , Issue 9, 2011, Pages 1375-1382

  Morales Serna, José Antonio ^a   García Ríos, Eréndira ^a   Bernal, Jorge ^a   Paleo, Ehecatl ^a   Gaviño, Rubén ^a   Cárdenas, Jorge ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

alcohol; benzotriazole esters; carbodiimide; carboxylic acids; reduction

Indexed keywords

ALCOHOLS; ESTERS; REDUCTION; SODIUM BOROHYDRIDE;

BENZOTRIAZOLES; CARBODIIMIDES; HIGH REACTIVITY; HYDROXYBENZOTRIAZOLE; IN-SITU FORMATIONS; PRESENCE OF WATER;

CARBOXYLIC ACIDS;

BENZOTRIAZOLE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; HYDROXYBENZOTRIAZOLE ESTER DERIVATIVE; SODIUM BOROHYDRIDE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; REDUCTION;

EID: 79955007469     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1259988     Document Type: Article

References (72)

1. Brown H C., Subba Rao B C., J. Am. Chem. Soc. 1956 78 2582
2. Periasamy M, Thirumalaikumar M J., J. Organomet. Chem. 2000 609 137
3. Yoon N M., Pak C S., Brown H C., Krishnamurthy S, Stocky T P., J. Org. Chem. 1973 38 2786
4. Brown H C., Stocky T P., J. Am. Chem. Soc. 1977 99 8218
5. Zhou Y, Gao G, Li H, Qu J, Tetrahedron Lett. 2008 49 3260
6. Chen M H., Iakovleva E, Kasten S, Magano J, Rodriguez D, Sexton K E., Zhang J, Lee H, Org. Prep. Proced. Int. 2002 34 665
7. Pridgen L N., Prol J Jr., Alexander B, Gillyard L, J. Org. Chem. 1989 54 3231
8. Bhaskar Kanth J V., Periasamy M, J. Org. Chem. 1991 56 5964
9. Bhanu Prasad A S., Bhaskar Kanth J V., Periasamy M, Tetrahedron 1992 48 4623
10. McKennon M J., Meyers A I., J. Org. Chem. 1993 58 3568
11. Haldar P, Guin J, Ray J K., Tetrahedron Lett. 2005 46 1071
12. Haldar P, Barman G, Ray J K., Tetrahedron 2007 63 3049
13. Kano S, Tanaka Y, Sugino E, Hibino S, Synthesis 1980 695
14. Itsuno S, Sakurai Y, Ito K, Synthesis 1988 995
15. Chen N, Yan S.-Q, Cui G.-Z, Wu S.-Z, J. Gansu Sci. 1996 8 86
16. Suseela Y, Periasamy M, Tetrahedron 1992 48 371
17. Abiko A, Masamune S, Tetrahedron Lett. 1992 33 5517
18. Cho S.-D, Park Y.-D, Kim J.-J, Falck J R., Yoon Y.-J, Bull. Korean Chem. Soc. 2004 25 407
19. Yan S.-Q, Sui H.-Z, Zhang Y.-L, J. Gansu Sci. 1996 8 71
20. Yang C, Pittman C U. Jr., Synth. Commun. 1998 28 2027
21. Hua-Jie Z, Pittman C U. Jr., Synth. Commun. 2003 33 1733
22. Tudge M, Mashima H, Savarin C, Humphrey G, Davies I, Tetrahedron Lett. 2008 49 1041
23. Ranu B C., Das A R., J. Chem. Soc., Perkin Trans. 1 1992 1561
24. Ranu B C., Synlett 1993 885
25. Narasimhan S, Madhavan S, Ganeshwar Prasad K, J. Org. Chem. 1995 60 5314
26. Narasimhan S, Madhavan S, Prasad K G., Synth. Commun. 1996 26 703
27. Zeynizadeh B, Zahmatkesh K, J. Chem. Res., Synop. 2003 522
28. Narasimhan S, Balakumar R, Synth. Commun. 2000 30 4387
29. Chen S, Xiao G.-M, Chen H.-R, Lou J.-Z, Chin. J. Pharm. 2006 37 807
30. Cai Z.-Y, Zhou W.-C, Chin. J. Pharm. 2007 38 177
31. Qiu Y.-C, Zhang F.-L, Zhang C.-N, Tetrahedron Lett. 2007 48 7595
32. Zhang J, Gao X, Zhang C, Ma J, Zhao D, Synth. Commun. 2009 39 1640
33. Giannis A, Sandhoff K, Angew. Chem., Int. Ed. Engl. 1989 28 218
34. Quagliato D A., Andrae P M., Matelan E M., J. Org. Chem. 2000 65 5037
35. Ravikumar K S., Chandrasekaran S, J. Org. Chem. 1996 61 826
36. Cha J S., Brown H C., J. Org. Chem. 1993 58 3914
37. Juszczyk P, Kasprzykowska R, Kolodziejczyk A S., Lett. Pept. Sci. 2003 10 79
38. Kamochi Y, Kudo T, Tetrahedron Lett. 2000 41 341
39. Matsubara K, Iura T, Maki T, Nagashima H, J. Org. Chem. 2002 67 4985
40. Behr A, Brehme V A., Adv. Synth. Catal. 2002 344 525
41. Drew M D., Lawrence N J., Fontaine D, Sehkri L, Synlett 1997 989
42. Fujisawa T, Mon T, Sato T, Chem. Lett. 1983 835
43. Kokotos G, Synthesis 1990 299
44. Mitra A K., De A, Karchaudhuri N, J. Indian Chem. Soc. 2003 80 923
45. Rodriguez M, Llinaero M, Doulet S, Heitz A, Martinez J, Tetrahedron Lett. 1991 32 923
46. Bandgar B P., Modhave R K., Wadgaonkar P P., Sande A R., J. Chem. Soc., Perkin Trans. 1 1996 1993
47. Ouerfelli O, Ishida M, Shinozaki H, Nakanishi K, Ohfune Y, Synlett 1993 409
48. Herbert J M., Hewson A T., Peace J E., Synth. Commun. 1998 28 823
49. Kokotos G, Noula C, J. Org. Chem. 1996 61 6994
50. Falorni M, Porcheddu A, Taddei M, Tetrahedron Lett. 1999 40 4395
51. Soai K, Yokoyama S, Mochida K, Synthesis 1987 647
52. Naqvi T, Bhattacharya M, Haq W, J. Chem. Res., Synop. 1999 424
53. Papavassilopoulou E, Christofis P, Terzoglou D, Minakakis P M., Tetrahedron Lett. 2007 48 8323
54. Tale R H., Patil K M., Dapurkar S E., Tetrahedron Lett. 2003 44 3427
55. Kim H.-O, Kahn M, Synlett 1999 1239
56. Hwang S.-H, Blaskovich M A., Kim H.-O, Open Org. Chem. J. 2008 2 107; http://www.benthamscience.com/open/toocj/index.htm
57. Suresh Babu V V., Kantharaju, Sudarshan N S., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2006 45 1880
58. Singh K N., Kaur A, Synth. Commun. 2005 35 2935
59. Falorni M, Giacomelli G, Porcheddu A, Taddei M A., J. Org. Chem. 1999 64 8962
60. McGearyl R P., Tetrahedron Lett. 1998 39 3319
61. Srivastava T, Srivastava T K., Haq W, Katti S B., J. Chem. Res., Synop. 2003 8 516
62. Cárdenas J, Morales-Serna J A., Sánchez E, Lomas L, Guerra N, Negrón G, ARKIVOC 2005 (vi) 428
63. Morales-Serna J A., Sánchez E, Velázquez R, Bernal J, García-Ríos E, Gaviño R, Negrón-Silva G, Cárdenas J, Org. Biomol. Chem. 2010 8 4940
64. Morales-Serna J A., Vera A, Paleo E, García-Ríos E, Gaviño R, García de la Mora G, Cárdenas J, Synthesis 2010 4261
65. Han S.-Y, Kim Y.-A, Tetrahedron 2004 60 2447
66. König W, Geiger R, Chem. Ber. 1970 103 788
67. Katritzky A R., Malhotra N, Fan W Q., Anders E, J. Chem. Soc., Perkin Trans. 2 1991 1545
68. Li P, Xu J C., J. Chem. Soc., Perkin Trans. 2 2001 113
69. Carpino L A., Ferrer F J., Org. Lett. 2001 3 2793
70. Chan L C., Cox B G., J. Org. Chem. 2007 72 8863
71. The enantiomeric purity of 6 was determined by NOE, employing the protocol previously described by our group:, Domínguez B E., García P E., Cárdenas J, Tetrahedron: Asymmetry 2005 16 3976
72. Luche J L., J. Am. Chem. Soc. 1978 100 2226