Efficient preparation of polyfunctional indoles via a zinc organometallic variation of the Fischer indole synthesis

Synthesis

Volumn , Issue 1, 2011, Pages 23-29

  Zhang, Zhi Guang ^a,b   Haag, Benjamin A ^a   Li, Jin Shan ^b   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b NANKAI UNIVERSITY   (China)

Author keywords

Fischer indole synthesis; indoles; N heterocycles; organozinc reagents; regioselectivity

Indexed keywords

ARYLDIAZONIUM SALTS; FISCHER INDOLE SYNTHESIS; FUNCTIONALIZED; INDOLES; N-HETEROCYCLES; ORGANOZINC REAGENTS;

FUNCTIONAL GROUPS; MICROWAVE IRRADIATION; ORGANOMETALLICS;

REGIOSELECTIVITY;

(4 ETHOXY 4 OZOBUTYL)ZINC BROMIDE; 1 (2,3 DIMETHYL 1H INDOL 5 YL)ETHANONE; 1 (2,3,4,9 TETRAHYDRO 1H CARBAZOL 6 YL)ETHANONE; 1,2,3,4 TETRAHYDROCYCLOPENTA[B]INDOL 7 YL PIVALATE; 2,3,4,9 TETRAHYDRO 1H CARBAZOLE 6 CARBONITRILE; 3 (2 ETHOXY 2 OXOETHYL) 2 METHYL 1H INDOL 5 YL PIVALATE; 5 BROMO 2,3 DIMETHYL 1H INDOLE; 5 FLUORO 2,3 DIMETHYL 1H INDOLE; 5 METHOXY 2,3 DIMETHYL 7 NITRO 1H INDOLE; 6 BROMO 2,3,4,9 TETRAHYDRO 1H CARBAZOLE; 6 METHOXY 2,3,4,9 TETRAHYDRO 1H CARBAZOLE; 6 METHOXY 8 NITRO 2,3,4,9 TETRAHYDRO 1H CARBAZOLE; 7 METHOXY 5 NITRO 1,2,3,4 TETRAHYDROCYCLOPENTA[B]INDOLE; CYCLOPENTYLZINC BROMIDE; DIAZONIUM COMPOUND; ETHYL (5 METHOXY 2 METHYL 1H INDOL 3 YL)ACETATE; ETHYL (5 METHOXY 7 NITRO 1H INDOL 3 YL)ACETATE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; IPRINDOLE; UNCLASSIFIED DRUG; ZINC; ZINC BROMIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; ISOMERISM; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 78650501807     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258348     Document Type: Article

References (24)

1. Sundberg R T., Indoles Academic Press London 1996
2. Comprehensive Heterocyclic Chemistry II Vol. 2 Katritzky A R. Rees C W. Scriven E F. V. Pergamon Press Oxford 1996 207-257
3. Sundberg R J., In Comprehensive Heterocyclic Chemistry II Vol. 2 Katritzky A R. Ress C W. Scriven E F. V. Bird C W. Pergamon Press Oxford 1996
4. Joule A, In Science of Synthesis Vol. 10 Thomas E J. Thieme Stuttgart 2000 Chap. 10.13
5. Humphrey G R., Kuethe J T., Chem. Rev. 2006 106 2875
6. Zeni G, Larock R C., Chem. Rev. 2004 104 2285
7. Cacchi S, Fabrizi G, Chem. Rev. 2005 105 2873
8. Fischer E, Jourdan F, Ber. Dtsch. Chem. Ges. 1883 16 2241
9. Robinson B, The Fischer Indole Synthesis Wiley-Interscience New York 1982
10. Handbook of Functionalized Organometallics Knochel P Wiley-VCH Weinheim 2005
11. Haag B A., Zhang Z.-G, Li J.-S, Knochel P, Angew. Chem. Int. Ed. 2010 49 in press; DOI: anie.201005319
12. Erdik E, Organozinc Reagents in Organic Synthesis CRC-Press Boca Raton 1996
13. Dong Z, Manolikakes G, Li J, Knochel P, Synthesis 2009 681
14. Despotopoulou C, Gignoux C, McConnell D, Knochel P, Synthesis 2009 3661
15. Monzon G, Knochel P, Synlett 2010 304
16. Metzger A, Argyo C, Knochel P, Synthesis 2010 882
17. Krasovskiy A, Malakhov V, Gavryushin A, Knochel P, Angew. Chem. Int. Ed. 2006 45 6040
18. Piller F M., Appukkuttan P, Gavryushin A, Helm M, Knochel P, Angew. Chem. Int. Ed. 2008 47 6802
19. Piller F M., Metzger A, Schade M A., Haag B A., Gavryushin A, Knochel P, Chem. Eur. J. 2009 15 7192
20. Haag B A., Peng Z, Knochel P, Org. Lett. 2009 11 4270
21. Sapountzis I, Knochel P, Angew. Chem. Int. Ed. 2004 43 897
22. Rice L M., Hertz E, Freed M E., J. Med. Chem. 1964 7 313
23. Baxter B L., Gluckman M I., Nature 1969 223 750
24. Chen J, Hu Y, Synth. Commun. 2006 36 1485