A short three-component synthesis of tricyclic compounds

Synlett

Volumn , Issue 2, 2003, Pages 241-243

  Hilt, Gerhard ^a   Korn, Tobias J ^a   Smolko, Konstantin I ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

Alkynes; Catalysis; Cobalt; Cyclization; Diels Alder reactions

Indexed keywords

BENZENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; SYNTHESIS;

EID: 0037287866     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-36795     Document Type: Article

References (14)

1. (a) Sonogashira, K. In Comprehensive Organic Synthesis, Vol. 3; Trost, B.; Flemming, I.; Pattenden, G., Eds.; Pergamon Press: New York, 1991, 521.
2. (b) Sonogashira, K. In Metal-catalyzed Cross-coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998, 203.
3. Besides secondary amines, primary amines such as tert-butylamine, also gave the propargylic amine product in this three component reaction, albeit in lower yields (46%).
4. (a) Martinelli, M. J.; Nayyar, N. K.; Moher, E. D.; Dhokte, U. P.; Pawlak, J. M.; Vaidyanathan, R. Org. Lett. 1999, 1, 447.
5. (b) The tosylation of propargylic alcohols (n = 1) under these conditions gave the desired products only in moderate yields (up to 25%) accompanied with the corresponding propargylic chloride in up to 35% yield and recovered starting material.
6. For recent cobalt(I)-catalyzed Diels-Alder reactions see: (a) Hilt, G.; Lüers, S.; Polborn, K. Isr. J. Chem. 2001, 41, 317.
7. (b) Hilt, G.; Smolko, K. I. Synthesis 2002, 686.
8. (c) Hilt, G.; Smolko, K. I. Synlett 2002, 1081.
9. 3S: m/z = 474.0864, found: m/z = 474.0811.
10. Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 300.
11. 20O: m/z = 240.1514, found: m/z = 240.1522.
12. (b) For a recent flexible synthesis of phenanthrene derivatives see: Fürstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264; and references cited therein.
13. Schlosser, M. In Organometallics in Synthesis; Wiley: Chichester, 1994, 129-133.
14. 20: m/z = 224.1565, found: m/z = 224.1572.