gem-Dibromomethyl aromatics: Efficient aldehyde equivalents in the Knoevenagel-Doebner reaction

Synthesis

Volumn , Issue 14, 2009, Pages 2349-2356

  Augustine, John Kallikat ^a,b   Naik, Yanjerappa Arthoba ^b   Poojari, Subba ^a   Chowdappa, Nagaraja ^a   Sherigara, Bailur Sheena ^b   Areppa, Kummara ^a  

^a SYNGENE INTERNATIONAL LTD   (India)

^b KUVEMPU UNIVERSITY   (India)

Author keywords

di tert butyl dicarbonate; gem dibromomethyl aromatics; Hydrolytic; Knoevenagel Doebner reaction; tert butyl cinnamates

Indexed keywords

CINNAMATES; DI-TERT-BUTYL DICARBONATE; DIBROMIDES; DICARBONATE; EFFICIENT SYNTHESIS; HYDROLYTIC; KNOEVENAGEL - DOEBNER REACTION; MALONIC ACID; ONE-POT SYNTHESIS; SINGLE-STEP; TERT-BUTYL CINNAMATES;

ALDEHYDES; AROMATIZATION; CARBOXYLIC ACIDS; ESTERIFICATION; ESTERS; SALTS;

GEMS;

3 BUTYL 3 (2 BROMOPYRIDIN 4 YL)PROP 2 ENOATE; 3 BUTYL 3 (3 BROMO 4 METHOXYPHENYL)PROP 2 ENOATE; 3 BUTYL 3 (4 METHOXY 2 NITROPHENYL)PROP 2 ENOATE; 3 BUTYL 3 (5 BROMO 2 CYANOPHENYL)PROP 2 ENOATE; 3 BUTYL 3 (5 CYANOPYRIDIN 2 YL)PROP 2 ENOATE; 3 BUTYL 3 (6 3 BUTOXY 5 NITROPYRIDIN 3 YL)PROP 2 ENOATE; 3 BUTYL 3 (6 BROMOPYRIDIN 3 YL)PROP 2 ENOATE; 3 BUTYL 3 (8 CHLOROQUINOLIN 2 YL)PROP 2 ENOATE; 3 BUTYL 3 [2 N 4 (4,4,5,5 TETRAMETHYL 1,3,2 DIOXABOROLAN 2 YL)PHENYL]PROP 2 ENOATE; 3 BUTYL 3 [6 CHLORO 4 (TRIFLUOROMETHYL)PYRIDIN 2 YL]PROP 2 ENOATE; 3 BUTYL CINNAMATE; ALDEHYDE; AROMATIC COMPOUND; BICARBONATE; CARBOXYLIC ACID DERIVATIVE; DI 3 BUTYL DICARBONATE; ESTER; GEM DIBROMOMETHYL; MALONIC ACID; METHYL 2 (3 3 BUTOXY 3 OXOPROP 1 ENYL)4 FLUOROBENZOATE; METHYL 4 (3 3 BUTOXY 3 OXOPROP 1 ENYL) 3 IODOBENZOATE; METHYL 4 (3 3 BUTOXY 3 OXOPROP 1 ENYL)NAPHTHALENE 1 CARBOXYLATE; METHYL 4 BROMO 3 (3 TERT BUTOXY 3 OXOPROP 1 ENYL)BENZOATE; METHYL 5 (3 3 BUTOXY 3 OXOPROP 1 ENYL)THIOPHENE 2 CARBOXYLATE; METHYL 5 BROMO 2 (3 3 BUTOXY 3 OXOPROP 1 ENYL)FURAN 3 CARBOXYLATE; METHYL 6 (3 3 BUTOXY 3 OXOPROP 1 ENYL) 2 CHLOROPYRIDINE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 67651083198     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216849     Document Type: Article

References (46)

1. Weinrich, K. P.; Heggs, R. P.; Northrup, V. M.; Ponce, E. M.; Balducci, J. J.; Weinstein, S.; Barcelon, S. A.; Rieger, M. WO 9,413,870, 1994.
2. (a) Song, J.; Hesse, M. Tetrahedron 1993, 49, 6797.
3. (b) Marquardt, U.; Schmid, D.; Jung, G. Synlett 2000, 1131.
4. (c) Callow, R. K.; Johnston, N. C. Bee World 1960, 41, 152.
5. Clifford, M. N.; Johnston, K. L.; Knigh, S.; Kuhnert, N. J. Agric. Food. Chem. 2003, 51, 2900.
6. Johnston, K. L.; Clifford, M. N.; Morgan, L. M. Am. J. Clin. Nutr. 2003, 79, 728.
7. Jassim, S. A. A.; Naji, M. A. J. Appl. Microbiol. 2003, 95, 412.
8. De Sotillo, D. R.; Hadley, M.; Wolf-Hall, C. J. Food Sci. 1998, 63, 907.
9. Bowels, B. L.; Miller, A. J. J. Food Sci. 1994, 59, 905.
10. For selected examples, see: (a) Maryanoff, B. E.; Reitz, A. B. Chem. Rev. 1989, 89, 863.
11. (b) Hatsuda, M.; Kuroda, T.; Seki, M. Synth. Commun. 2003, 33, 427.
12. (c) Kisanga, P.; 'Sa, B. D.; Verkade, J. Tetrahedron 2001, 57, 8047.
13. (d) Herrmann, W. A.; Wang, M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1641;
14. Angew. Chem. 1991, 103, 1709.
15. (e) Ledford, B. E.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 8125.
16. (f) Barma, D. K.; Kundu, A.; Bandyopadhyay, A.; Sangras, B.; Briot, A.; Mioskowski, R.; Falck, J. R. Tetrahedron Lett. 2004, 45, 5917.
17. (g) Taguchi, H.; Shimoji, K.; Yamamoto, H.; Nozaki, H. Bull. Chem. Soc. Jpn. 1974, 47, 2529.
18. (h) Matui, S.; Tanaka, K.; Kaji, A. Synthesis 1983, 127.
19. (i) Huang, Y.; Shen, Y.; Chen, C. Tetrahedron Lett. 1986, 27, 2903.
20. (j) Olah, G. A.; Wu, A. H.; Farooq, O.; Prakash, G. K. Synthesis 1988, 537.
21. 3PO, see p. 7 in: Hermeling, D.; Bassler, P.; Hammes, P.; Hugo, R.; Lechtken, P.; Siegel, H. EP 0638580, 1995.
22. (a) Horner, L.; Hoffmann, H. M. R.; Wippel, H. G. Chem. Ber. 1958, 91, 61.
23. (b) Wadsworth, W. S. Jr.; Emmons, W. D. Org. Synth. Coll. Vol. V; John Wiley & Sons: London, 1973, 547.
24. (c) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873.
25. (d) Ando, K. J. Org. Chem. 1997, 62, 1934.
26. (a) Galat, A. J. Am. Chem. Soc. 1946, 68, 376.
27. (b) Martin, C. J.; Schepartz, A. I.; Daubert, B. F. J. Am. Chem. Soc. 1948, 70, 2601.
28. (c) Klein, J.; Bergmann, E. D. J. Am. Chem. Soc. 1957, 79, 3452.
29. Augustine, J. K.; Naik, Y. A.; Mandal, A. B.; Chowdappa, N.; Praveen, V. B. J. Org. Chem. 2007, 72, 9854.
30. For selected examples, see: (a) Larock, R. C. Comprehensive Organic Transformations, 2nd Ed.; John Wiley & Sons: Chichester, 1999, 1224.
31. (b) Chung, S. J.; Kim, D. H. Tetrahedron 1995, 51, 12549.
32. (c) Sander, W.; Exner, M. J. Chem. Soc., Perkin Trans. 2 1999, 2285.
33. (d) Tabushi, I.; Sasaki, T. Tetrahedron Lett. 1982, 23, 1913.
34. (e) Dann, O.; Char, H.; Griessmeier, H. Liebigs Ann. Chem. 1982, 1836.
35. (f) Li, W.; Li, J.; DeVincentis, D.; Mansour, T. S. Tetrahedron Lett. 2004, 45, 1071.
36. (g) Coleman, G. H.; Honeywell, G. E. Org. Synth. Coll. Vol. II; John Wiley & Sons: London, 1943, 98-91.
37. (h) Bankston, D. Synthesis 2004, 282.
38. (i) Gillespie, J. S.; Acharya, S. P.; Shamblee, D. A.; Davis, R. E. Tetrahedron 1975, 31, 3.
39. (j) Zondervan, C.; Beuken, E.; Kooijman, H.; Spek, A. L.; Feringa, B. L. Tetrahedron Lett. 1997, 38, 3111.
40. (k) Helms, A.; Heiler, D.; McLendon, G. J. Am. Chem. Soc. 1992, 114, 6227.
41. (l) Waehaelae, K.; Ojanperae, I.; Haeyri, L.; Hase, T. A. Synth. Commun. 1987, 17, 137.
42. (m) Man, Y.-M.; Thomas, C. W.; Wong, H. N. C. J. Org. Chem. 1990, 55, 3214.
43. (n) Jung, M. E.; Hogan, K. T. Tetrahedron Lett. 1988, 29, 6199.
44. Mandal, A. B.; Augustine, J. K.; Quattropani, A.; Bombrun, A. Tetrahedron Lett. 2005, 46, 6033.
45. Takeda, K.; Akiyama, A.; Nakamura, H.; Takizawa, S.; Mizuno, Y.; Takayanagi, H.; Harigaya, Y. Synthesis 1994, 1063.
46. Srinivas, K. V. N. S.; Mahender, I.; Das, B. Synthesis 2003, 2479.