Pd/C-catalyzed reductive formylation of indoles and quinolines using formic acid

Synthesis

Volumn , Issue 8, 2011, Pages 1227-1232

  Kulkarni, Aditya ^a   Gianatassio, Ryan ^a   Török, Béla ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

Catalytic transfer hydrogenation; Domino reaction; Formylation; Indoles; Quinolines

Indexed keywords

CATALYTIC TRANSFER HYDROGENATION; DOMINO REACTIONS; FORMYLATION; INDOLES; QUINOLINES;

CATALYSIS; HYDROGENATION; REACTION KINETICS;

FORMIC ACID;

2 METHYLINDOLINE 1 CARBALDEHYDE; 3,4 DIHYDROQUINOLINE 1 [2H]CARBALDEHYDE; 3,4 DIHYDROQUINOLINE 2 [2H]CARBALDEHYDE; 5 FLUOROINDOLINE 1 CARBALDEHYDE; 5 METHOXYINDOLINE 1 CARBALDEHYDE; 5 METHYLINDOLINE 1 CARBALDEHYDE; 6 HYDROXY 3,4 DIHYDROQUINOLINE 1 [2H]CARBALDEHYDE; 6 METHOXY 3,4 DIHYDROQUINOLINE 1 [2H]CARBALDEHYDE; 6 METHYL 3,4 DIHYDROQUINOLINE 1 [2H]CARBALDEHYDE; 7 METHYLINDOLINE 1 CARBALDEHYDE; ETHYL 1 FORMYLINDOLINE 2 CARBOXYLATE; FORMIC ACID; INDOLE DERIVATIVE; INDOLINE 1 CARBALDEHYDE; N FORMYLINDOLINE DERIVATIVE; N FORMYLTETRAHYDROQUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; DOMINO REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROFORMYLATION; HYDROGENATION; TEMPERATURE SENSITIVITY;

EID: 79953799114     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1259978     Document Type: Article

References (25)

1. Rakhit A, Hurley M E., Tipnis V, Coleman J, Rommel A, Brunner H R., J. Clin. Pharmacol. 1986 26 156
2. Boger D L., Boyce C W., Garbaccio R M., Goldberg J A., Chem. Rev. 1997 97 787
3. Kim W G., Kim J P., Koshino H, Shin-Ya K, Seto H, Yoo I D., Tetrahedron 1997 53 4309
4. Gruenfeld N, Stanton J L., Yuan A M., Ebetino F H., Browne L J., Gude C, Huebner C F., J. Med. Chem. 1983 26 1277
5. Anas S, Kagan H B., Tetrahedron: Asymmetry 2009 20 2193
6. Liu D, Zhao G, Xiang L, Eur. J. Org. Chem. 2010 3975
7. Wolfe J P., Rennels R A., Buchwald S L., Tetrahedron 1996 52 7525
8. Yang B H., Buchwald S L., Org. Lett. 1999 1 35
9. Wagaw S, Rennels R A., Buchwald S L., J. Am. Chem. Soc. 1997 119 8451
10. Houlden C E., Bailey C D., Ford J G., Gagné M R., Lloyd-Jones G C., Booker-Milburn K I., J. Am. Chem. Soc. 2008 130 10066
11. Klapars A, Huang X, Buchwald S L., J. Am. Chem. Soc. 2002 124 7421
12. Ganton M D., Kerr M A., Org. Lett. 2005 7 4777
13. Gilchrist T L., Graham K, Tetrahedron 1997 53 791
14. Tan M, Zhang Y, Tetrahedron Lett. 2009 50 4912
15. Bandini M, Eichholzer A, Angew. Chem. Int. Ed. 2009 48 9608
16. Michael J P., Nat. Prod. Rep. 2007 24 223
17. Fukuda T, Mine Y, Iwao M, Tetrahedron 2001 57 975
18. Somei M, Saida Y, Funamoto T, Ohta T, Chem. Pharm. Bull. 1987 35 3146
19. Yamada Y, Arima S, Okada C, Akiba A, Kai T, Hariyaga Y, Chem. Pharm. Bull. 2006 54 788
20. Ciske F L., Barbachyn M R., Genin M J., Grega K C., Lee C S., Dolak L A., Seest E P., Watt W, Adams W J., Friis J M., Ford C W., Zurenko G E., Bioorg. Med. Chem. Lett. 2003 13 4235
21. Bartk M, Molnr, Heterogeneous Catalytic Hydrogenation, In The Chemistry of Functional Groups Suppl. A3 Patai S Wiley Chichester 1997 Chap. 16 843
22. Smith G V., Notheisz F, Heterogeneous Catalysis in Organic Chemistry Academic Press San Diego 1999
23. Kulkarni A, Török B, Curr. Org. Synth. 2011 8 187
24. Kikugawa Y, Kashimura M, Synthesis 1982 785
25. Abraham R J., Byrne J J., Griffiths L, Perez M, Magn. Reson. Chem. 2006 44 491