Conjugate addition - SNAr domino reaction for the synthesis of benzo- or pyridyl-fused lactams and sultams

Synthesis

Volumn , Issue 24, 2010, Pages 4273-4281

  Nørager, Niels Grøn ^a,b   Juhl, Karsten ^a  

^a H LUNDBECK A S   (Denmark)

^b AARHUS UNIVERSITY   (Denmark)

Author keywords

bicyclic compounds; domino reactions; heterocycles; Michael addition; nucleophilic aromatic substitution

Indexed keywords

BICYCLIC COMPOUNDS; DOMINO REACTIONS; HETEROCYCLES; MICHAEL ADDITIONS; NUCLEOPHILIC AROMATIC SUBSTITUTION;

AMIDES; AROMATIC COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ADDITION REACTIONS;

2 FLUORO 3 METHOXY N PHENYLBENZAMIDE; 2 FLUORO N METHYLBENZAMIDE; 2 FLUORO N METHYLBENZENESULFONAMIDE; 2 FLUORO N PHENYLBENZAMIDE; 2 FLUORO N PHENYLBENZENESULFONAMIDE; 2 FLUORO N PHENYLNICOTINAMIDE; 2 FLUOROPYRIDINE 3 SULFONIC ACID PHENYLAMIDE; 2 FLUOROPYRIDINE 3 SULFONYL CHLORIDE; 2,6 DIFLUORO N PHENYLBENZENESULFONAMIDE; 3 CHLORO 5 FLUORONICOTINIC ACID; 3 FLUORO N PHENYLNICOTINAMIDE; CHEMICAL COMPOUND; ETHYL 1 OXO 2,3 DIPHENYL 1,2 DIHYDRO 2,6 NAPHTHYRIDINE 4 CARBOXYLATE; ETHYL 1 OXO 2,3 DIPHENYL 1,2 DIHYDROISOQUINOLINE 4 CARBOXYLATE; ETHYL 1,1 DIOXO 2,3 DIPHENYL 1,2 DIHYDRO 1(6) THIA 2,5 DIAZANAPHTHALENE 4 CARBOXYLATE; ETHYL 2 (TERT BUTOXYCARBONYLPROPYLAMINO) 3 METHYL 1 OXO 1,2 DIHYDRO 2,6 NAPHTHYRIDINE 4 CARBOXYLATE; ETHYL 2 (TERT BUTOXYCARBONYLPROPYLAMINO) 8 CHLORO 3 METHYL 1 OXO 1,2 DIHYDRO 2,6 NAPHTHYRIDINE 4 CARBOXYLATE; ETHYL 2 (TERT BUTOXYCARBONYLPROPYLAMINO) 8 FLUORO 3 METHYL 1 OXO 1,2 DIHYDRO 2,6 NAPHTHYRIDINE 4 CARBOXYLATE; ETHYL 2 METHYL 1 OXO 3 PHENYL 1,2 DIHYDROISOQUINOLINE 4 CARBOXYLATE; ETHYL 5 METHOXY 1 OXO 2,3 DIPHENYL 1,2 DIHYDROISOQUINOLINE 4 CARBOXYLATE; ETHYL 5 OXO 6,7 DIPHENYL 5,6 DIHYDRO 1,6 NAPHTHYRIDINE 8 CARBOXYLATE; ETHYL 7 METHYL 5 OXO 6 PHENYL 5,6 DIHYDRO 1,6 NAPHTHYRIDINE 8 CARBOXYLATE; LACTAM DERIVATIVE; SULTAM DERIVATIVE; TERT BUTYL 7 METHYL 5 OXO 6 PHENYL 5,6 DIHYDRO 1,6 NAPHTHYRIDINE 8 CARBOXYLATE; TERT BUTYL N PROPYLHYDRAZINECARBOXYLATE; TERT BUTYL N' (3 CHLORO 5 FLUOROPYRIDINE 4 CARBONYL) N PROPYLHYDRAZINECARBOXYLATE; TERT BUTYL N' (3 FLUOROPYRIDINE 4 CARBONYL) N PROPYLHYDRAZINECARBOXYLATE; TERT BUTYL N' (3,5 DIFLUOROPYRIDINE 4 CARBONYL) N PROPYLHYDRAZINECARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATE ADDITION; DOMINO REACTION; PROTON TRANSPORT; SYNTHESIS;

EID: 78650171861     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258302     Document Type: Article

References (32)

1. For reviews on domino reactions, see:, Padwa A, Bur S K., Tetrahedron 2007 63 5341
2. Padwa A, Pure Appl. Chem. 2004 76 1933
3. Tietze L F., Chem. Rev. 1996 96 115
4. Tietze L F., Angew. Chem., Int. Ed. Engl. 1993 32 131
5. Bentley K W., Nat. Prod. Rep. 2000 17 247
6. Glushkov V A., Shklyaev Y V., Chem. Heterocycl. Compd. 2001 37 663
7. Pettit G R., Meng Y H., Herald D L., Graham K A. N., Pettit R K., Doubek D L., J. Nat. Prod. 2003 66 1065
8. Simonsen K B., Juhl K, Steiniger-Brach B, Nielsen S M., Curr. Opin. Drug Discovery Dev. 2010 13 379
9. Jayaraman M, Fox B M., Hollingshead M, Kohlhagen G, Pommier Y, Cushman M, J. Med. Chem. 2000 43 3688
10. Busch U, Heinzel G, Narjes H, Nehmiz G, J. Clin. Pharmacol. 1996 36 1771
11. Zia-ur-Rehman M, Choudary J A., Ahmad S, Bull. Korean Chem. Soc. 2005 26 1771
12. Lombardino J G., Wiseman E H., McLamore W M., [nl]J. Med. Chem. 1971 14 1171
13. See for example:, Modi A R., Usgaonkar R N., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1979 18 304
14. Fisher L E., Muchowski J M., Clark R D., J. Org. Chem. 1992 57 2700
15. Davis S E., Church A C., Griffith C L., Beam C F., Synth. Commun. 1997 27 2961
16. Jagtap P G., Baloglu E, Southan G, Williams W, Roy A, Nivorozhkin A, Landrau N, Desisto K, Salzman A L., Szabo C, Org. Lett. 2005 7 1753
17. Coelho F, Veronese D, Lopes E C. S., Rossi R C., Tetrahedron Lett. 2003 44 5731
18. Saeed A, Ashraf Z, Pharm. Chem. J. 2008 42 277
19. See for example:, Snow R J., Butz T, Hammach A, Kapadia S, Morwick T M., Prokopowisc A S., Takahashi H, Tan J D., Tschantz M A., Wang X.-J, Tetrahedron Lett. 2002 43 7553
20. Guastavino J F., Barolo S M., Rossi R A., Eur. J. Org. Chem. 2006 3898
21. See for example:, Alonso F, Belatskaya I P., Yus M, Chem. Rev. 2004 104 3079
22. Nakamura I, Yamamoto Y, Chem. Rev. 2004 104 2127
23. Wang F, Liu H, Fu H, Jiang Y, Zhao Y, Org. Lett. 2009 11 2469
24. Wang H, Gao K, Jiang Y, Ma D, Heterocycles 2009 79 695
25. Zheng Z, Alper H, Org. Lett. 2008 10 4903
26. Zia-ur-Rehman M, Choudary J A., Elsegood M R. J., Siddiqui H L., Kahn K M., Eur. J. Med. Chem. 2009 44 1311
27. Lucilia M, daMata E N., Motherwell W B., Ujjainwalla F, Tetrahedron Lett. 1997 38 137
28. Rayabarapu D K., Zhou A, Jeon K O., Samarakoon T, Rolfe A, Siddiqui H, Hanson P R., Tetrahedron 2009 65 3180
29. Goossen L J., Manjolinho F, Khan B A., Rodriguez N, J. Org. Chem. 2009 74 2620
30. Meyer K G., Synlett 2004 2355
31. Bouillon A, Lancelot J.-C, Collot V, Bovy P R., Rault S, Tetrahedron 2002 58 3323
32. Gupta L, Hoepker A C., Singh K J., Collum D B., [nl]J. Org. Chem. 2009 74 2231