Novel syntheses of α-morpholinoamides from α,α-dichloroacetamides

Journal of Organic Chemistry

Volumn 67, Issue 23, 2002, Pages 8239-8242

  Katritzky, Alan R ^a   Zhang, Yuming ^a   Singh, Sandeep K ^a  

^a University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INTERMEDIATES;

ETHERS; HEATING; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

2 (1H 1,2,3 BENZOTRIAZOL 1 YL) 2 MORPHOLINO N (1 PHENYLETHYL)ACETAMIDE; 2 (1H 1,2,3 BENZOTRIAZOL 1 YL) N BENZYL 2 MORPHOLINOACETAMIDE; ACETAMIDE DERIVATIVE; ALPHA MORPHOLINOAMIDE DERIVATIVE; ALPHA,ALPHA DICHLOROACETAMIDE; ANTICONVULSIVE AGENT; ANTIINFECTIVE AGENT; ANTIINFLAMMATORY AGENT; MORPHOLINE DERIVATIVE; NEUROPROTECTIVE AGENT; UNCLASSIFIED DRUG; 2,2 DICHLOROACETAMIDE; 2,2-DICHLOROACETAMIDE; AMIDE; BENZOTRIAZOLE; TRIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HEATING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; CHEMISTRY; SYNTHESIS;

ACETAMIDES; AMIDES; MORPHOLINES; TRIAZOLES;

EID: 0037111785     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020335u     Document Type: Article

References (39)

1. Marcincal-Lefebvre, A.; Gesquiere, J. C.; Lemer, C.; Dupuis, B. J. Med. Chem. 1981, 24, 889.
2. Joshi, K. C.; Pathak, V. N.; Jain, S. K. Pharmazie 1980, 35, 667.
3. Bachir, M.; Riffaud, J.-P.; Lacolle, J.-Y.; Lemoine, J.; De Almeida, A.; Houziaux, P.; Danree, B. Eur. J. Med. Chem. 1990, 25, 71.
4. Oshiro, Y.; Sakurai, Y.; Tanaka, T.; Kikuchi, T.; Hirose, T.; Tottori, K. J. Med. Chem. 1991, 34, 2014.
5. (a) Malatesta, P.; Migliaccio, G.; Aliberti, U. Farmaco Ed. Sci. 1962, 17, 601; Chem. Abstr. 1963, 58, 1377h.
6. (a) Malatesta, P.; Migliaccio, G.; Aliberti, U. Farmaco Ed. Sci. 1962, 17, 601; Chem. Abstr. 1963, 58, 1377h.
7. (b) Abbady, M. A.; Abde-Hafez, Sh. H. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 160, 121; Chem. Abstr. 2000, 133, 150649x.
8. (b) Abbady, M. A.; Abde-Hafez, Sh. H. Phosphorus, Sulfur Silicon Relat. Elem. 2000, 160, 121; Chem. Abstr. 2000, 133, 150649x.
9. (c) Shafeeque, S.; Mohan, S.; Manjunatha, K. S. Ind. J. Heterocycl. Chem. 1999, 8, 297; Chem. Abstr. 1999, 131, 170237y.
10. (c) Shafeeque, S.; Mohan, S.; Manjunatha, K. S. Ind. J. Heterocycl. Chem. 1999, 8, 297; Chem. Abstr. 1999, 131, 170237y.
11. (d) Padia, J. K.; Patel, P. B. J. Inst. Chem. (India) 1989, 61, 109 ; Chem. Abstr. 1991, 114, 23513f
12. (d) Padia, J. K.; Patel, P. B. J. Inst. Chem. (India) 1989, 61, 109 ; Chem. Abstr. 1991, 114, 23513f
13. (a) Bergman, J.; Brimert, T. Acta Chem. Scand. 1999, 53, 48; Chem. Abstr. 1999, 130, 237422e.
14. (a) Bergman, J.; Brimert, T. Acta Chem. Scand. 1999, 53, 48; Chem. Abstr. 1999, 130, 237422e.
15. (b) Ismail, M. F.; Enayat, E. I.; El Bassiouny, F. A. A.; Younis, H. A. Acta Chim. Hung. 1991, 128, 365; Chem. Abstr. 1991, 115, 158859q.
16. (b) Ismail, M. F.; Enayat, E. I.; El Bassiouny, F. A. A.; Younis, H. A. Acta Chim. Hung. 1991, 128, 365; Chem. Abstr. 1991, 115, 158859q.
17. (c) Katritzky, A. R.; Lan, X.; Yang, J.; Denisko, O. Chem. Rev. 1998, 98, 409.
18. Katritzky, A. R.; Cui, X.-L.; Yang, B.; Steel, P. J. J. Org. Chem. 1999, 64, 1979.
19. Katritzky, A. R.; Qui, G.; He, H.-Y.; Yang, B. J. Org. Chem. 2000, 65, 3683.
20. Katritzky, A. R.; Bayyuk, S. I.; Rachwal, S. Synthesis 1991, 279.
21. Isshiki, T.; Kuwada, Y. J. Pharm. Soc. Jpn. 1952, 72, 72; Chem. Abstr. 1952, 46, 11147.
22. Isshiki, T.; Kuwada, Y. J. Pharm. Soc. Jpn. 1952, 72, 72; Chem. Abstr. 1952, 46, 11147.
23. (a) Bolton, G. L.; Hodges, J. C.; Rubin, J. R. Tetrahedron 1997, 53, 6611.
24. (10b) Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606.
25. (a) Yamamoto, Y.; Ito, W. Tetrahedron 1988, 44, 5415.
26. (b) Fang, X.; Johannsen, M.; Yao, S.; Gathergood, N.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1999, 64, 4844.
27. (a) Singh, R. P.; Cao, G.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1999, 64, 2873.
28. (b) Shen, Y.; Zhang, Y.; Zhou, Y. J. Chem. Soc., Perkin Trans. 1 1999, 1759.
29. Kitamura, T.; Harano, K.; Hisano, T. Chem. Pharm. Bull. 1992, 40, 2255.
30. (a) Wojciechowski, K. Tetrahedron 1993, 49, 7277.
31. (b) Dufour, M.; Gramain, J.-C.; Husson, H.-P.; Sinibaldi, M.-E.; Troin, Y. J. Org. Chem. 1990, 55, 5485.
32. (c) Gardette, D.; Gramain, J.-C.; Sinibaldi, M.-E. Heterocycles 1990, 31, 1439.
33. (d) Gramain, J.; Husson, H.-P.; Troin, Y. J. Org. Chem. 1985, 50, 5517.
34. (a) Katritzky, A. R.; Urogdi, L.; Mayence, A. Synthesis 1989, 323.
35. (b) Katritzky, A. R.; Odens, H. H.; Voronkov, M. V. J. Org. Chem. 2000, 65, 1886.
36. (c) Katritzky, A. R.; Mehta, S.; He, H.-Y.; Cui, X. J. Org. Chem. 2000, 65, 4364.
37. Ghosez, L.; Rossey, G.; Didderen, F.; Ger. Offen. 2 623 226; Chem. Abstr. 1977, 86, 120998d.
38. Shah, K. J.; Trivedi, J. J. Indian J. Appl. Chem. 1967, 30, 11; Chem. Abstr. 1968, 68, 59230 g.
39. Shah, K. J.; Trivedi, J. J. Indian J. Appl. Chem. 1967, 30, 11; Chem. Abstr. 1968, 68, 59230 g.