An efficient multicomponent synthesis of polysubstituted pyrrolidines and tetrahydropyrimidines starting directly from nitro compounds in water

Synthesis

Volumn , Issue 16, 2010, Pages 2823-2827

  Das, Biswanath ^a   Shinde, Digambar Balaji ^a   Kanth, Boddu Shashi ^a   Satyalakshmi, Gandham ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Multicomponent synthesis; Nitro compounds; Pyrrolidines; Reactions in water; Tetrahydropyrimidines

Indexed keywords

DIALKYL ACETYLENEDICARBOXYLATES; HIGH YIELD; MOLAR RATIO; MULTICOMPONENT SYNTHESIS; NITRO COMPOUNDS; NITROARENES; POLYSUBSTITUTED PYRROLIDINES; PYRROLIDINES; REACTIONS IN WATER; REDUCTION OF NITRO COMPOUNDS; ROOM TEMPERATURE; THREE COMPONENT REACTIONS;

FORMALDEHYDE; SYNTHESIS (CHEMICAL);

COMPLEXATION;

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; AROMATIC NITRO COMPOUND; CARBOXYLIC ACID DERIVATIVE; DIETHYL 1,3 BIS[4 (TRIFLUOROMETHYL)PHENYL] 1,2,3,6 TETRAHYDROPYRIMIDINE 4,5 DICARBOXYLATE; DIMETHYL 1,3 BIS(4 METHOXYPHENYL) 1,2,3,6 TETRAHYDROPYRIMIDINE 4,5 DICARBOXYLATE; DIMETHYL 1,3 BIS[4 (TRIFLUOROMETHYL)PHENYL] 1,2,3,6 TETRAHYDROPYRIMIDINE 4,5 DICARBOXYLATE; DIMETHYL 1,3 DI(4 TOLYL) 1,2,3,6 TETRAHYDROPYRIMIDINE 4,5 DICARBOXYLATE; ETHYL 3 ETHOXYMETHYL 1 (3 METHYLPHENYL) 4,5 DIOXOPYRROLIDONE 3 CARBOXYLATE; ETHYL 3 ETHOXYMETHYL 1 PHENYL 4,5 DIOXOPYRROLIDONE 3 CARBOXYLATE; FORMALDEHYDE; METHYL 1 (4 HYDROXYPHENYL) 3 METHOXYMETHYL 4,5 DIOXOPYRROLIDONE 3 CARBOXYLATE; METHYL 1 (4 TRIFLUOROMETHYLPHENYL) 3 METHOXYMETHYL 4,5 DIOXOPYRROLIDONE 3 CARBOXYLATE; METHYL 3 METHOXYMETHYL 1 (3 METHYLPHENYL) 4,5 DIOXOPYRROLIDONE 3 CARBOXYLATE; NITRO DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; TETRAHYDROPYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROCESS DEVELOPMENT; REACTION TIME; ROOM TEMPERATURE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 77955387924     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258138     Document Type: Article

References (19)

1. Janecki T, Blaszczyk E, Studzian K, Janecka A, Krajenska U, Rozalski M, J. Med. Chem. 2005 48 3516
2. Hong C Y., Kim Y K., Chang J H., Kim S H., Choi H, Nam D H., Kim Y Z., Kwak J H., J. Med. Chem. 1997 40 3584
3. Raj A A., Raghunathan R, SrideviKumari M R., Raman N, Bioorg. Med. Chem. 2003 11 407
4. Nair V, Chi G, Ptak R, Neamati N, J. Med. Chem. 2006 49 445
5. Pattarimi P, Smeyne R J., Morgan J I., Neuroscience 2007 145 654
6. Messer W S. Jr., Abuh Y F., Paryasamy S, Ngur D O., Edger M A. N., Eissadi A A., Sheih S, Dunbar P G., Roknich S, Rho T, Fang Z, Ojo B, Zhang H, Huzl J J., Nagy P I., J. Med. Chem. 1997 40 1230
7. Tozkoparan B, Yarim M, Sarac S, Ertan M, Kelicun P, Altinoc G, Demirdamar R, Arch. Pharm. Pharm. Med. Chem. 2000 333 415
8. For recent examples of multicomponent reactions, see:, Ohno H, Ohta Y, Oishi S, Fujii N, Angew. Chem. Int. Ed. 2007 46 2295
9. Komagawa S, Saito S, Angew. Chem. Int. Ed. 2006 45 2446
10. Yoshida H, Fukushima H, Ohshita J, Kunai A, J. Am. Chem. Soc. 2006 128 11040
11. Dondas H, Fishwick C W. G., Gai X, Grigg R, Kilner C, Dumrongchai N, Kongkathip B, Kongkathip N, Polysuk C, Sridharan V, Angew. Chem. Int. Ed. 2005 44 7570
12. Pache S, Lautens M, Org. Lett. 2003 5 4827
13. Cao H, Jiang H.-F, Qi C.-R, Yao W.-J, Chem H.-J, Tetrahedron Lett. 2009 50 1209
14. Srikrishna A., Sridharan M., Prasad K. R.; Tetrahedron; 2010, 66: in press; DOI: 10.1016/ j.tet.2010.03.084
15. Das B, Banerjee J, Mahender G, Majhi A, Org. Lett. 2004 6 3349
16. Das B, Holla H, Venkateswalu K, Majhi A, Tetrahedron Lett. 2005 46 8895
17. Das B, Satyalakshmi G, Suneel K, Shashikanth B, Tetrahedron Lett. 2008 49 7209
18. Ranu B C., Eur. J. Org. Chem. 2000 2347
19. Lee J C., Choi K I. I., Koh H Y., Kang Y, Kuin Y, Kang Y, Cho Y S., Synthesis 2001 81