One-pot synthesis of functionalized indoles by cyclization of lithiated amides and nitriles with oxaldiimidoyl dichlorides

European Journal of Organic Chemistry

Volumn , Issue 20, 2001, Pages 3953-3959

  Langer, Peter ^a   Anders, Joachim T ^a   Döring, Manfred ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Amides; Cyclization; Indoles; Nitrogen heterocycles

Indexed keywords

(3 IMINO 2,3 DIHYDRO 1H INDOL 2 YLIDENE)ACETAMIDE DERIVATIVE; 3 IMINOINDOLE DERIVATIVE; AMIDE; ANION; BENZYL CYANIDE DERIVATIVE; BIS(IMIDOYL)CHLORIDE DERIVATIVE; CHLORINE DERIVATIVE; INDOLE DERIVATIVE; NITRILE; OXALDIIMIDOYL DICHLORIDE DERIVATIVE; OXALIC ACID BIS(IMIDOYL)CHLORIDE DERIVATIVE; OXALIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034770315     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200110)2001:20<3953::AID-EJOC3953>3.0.CO;2-H     Document Type: Article

References (12)

1. [1a]S. Blechert, R. Knier, H. Schroers, T. Wirth, Synthesis 1995, 592-604.
2. [1b] U. Pindur, M. Rogge, M. Rehn, W. Massa, B. Peschel, J. Heterocycl. Chem. 1994, 31, 981 and references therein.
3. [1c] J. Lévy, J. Sapi, J.-Y. Laronze, D. Royer, L. Toupet, Synlett 1992, 601-602.
4. To date, previous syntheses of 2-alkylidene-3-oxindoles utilized the aldol reaction of 3-oxindoles: Using this approach, ester-substituted 3-oxindoles were obtained with good stereoselectivities but low yields (12-44% yield). The aldolization with benzaldehyde derivatives proceeded with low stereocontrol: [2a] J.-Y. Mérour, L. Chichereau, E. Desarbre, P. Gadonneix, Synthesis 1996, 519-524.
5. [5a] For the Heck-reaction of iodoanilines with alkynes in the presence of CO, see: [2b] E. Brocato, C. Castagnoli, M. Catellani, G. P. Chiusoli, Tetrahedron Lett. 1992, 33, 7433-7436.
6. E. Wenkert, S. Liu, Synthesis 1992, 323-327.
7. R. Stahl, R. Galli, R. Güller, H.-J. Borschberg, Helv. Chim. Acta 1994, 77, 2125-2132.
8. [5a] A. Buzas, J.-Y. Mérour, Synthesis 1989, 458-461.
9. [5b] J.-Y. Mérour, A. Mérour, Synthesis 1994, 767-769.
10. Y. Davion, B. Joseph, J.-Y. Mérour, Synlett 1998, 1051-1052.
11. P. Langer, J. Wuckelt, M. Döring, H. Görls, J. Org. Chem. 2000, 65, 3603-3611.
12. P. Langer, M. Döring, H. Görls, unpublished results.