Syntheses of 2-benzylsubstituted imidazo[1,2-a]pyrimidines via coupling-cyclization under Pd-Cu catalysis

Letters in Organic Chemistry

Volumn 8, Issue 6, 2011, Pages 401-405

  Bakherad, Mohammad ^a   Keivanloo, Ali ^a   Mohammadi, Marzieh ^a   Jajarmi, Saeideh ^a  

^a SHAHROOD UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Aryl iodide; Imidazo 1,2 a pyrimidines; Pd catalyzed; Sonogashira coupling

Indexed keywords

EID: 79961060603     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811796064368     Document Type: Article

References (24)

1. Sonogashira, K. Development of Pd-Cu catalyzed crosscoupling of terminal acetylenes with sp2-carbon halides. J. Organomet. Chem. 2002, 653, 46-49 (Pubitemid 34594497)
2. Chinchilla, R.; Najera, C. The Sonogashira Reaction: A Booming methodology in Synthetic Organic Chemistry. Chem. Rev. 2007, 107, 874-922. (Pubitemid 46504819)
3. Toyota, M.; Komori, C.; Ihara, M. A Concise Formal Total Synthesis of Mappicine and Nothapodytine B via an Intramolecular Hetero Diels-Alder Reaction. J. Org. Chem., 2000, 65, 7110-7113
4. Yoshimura, F.; Kawata, S.; Hirama, M. Synthetic study of kedarcidin chromophore: atropselective construction of the ansamacrolide. Tetrahedron Lett., 1999, 40, 8281-8285 (Pubitemid 29507070)
5. Miller, M. W.; Johnson, C. R. Sonogashira Coupling of 2-Iodo-2-cycloalkenones: Synthesis of (+)- and (-)-Harveynone and (-)-Tricholomenyn. J. Org. Chem., 1997, 62, 1582-1585
6. Sakai, A.; Aoyama, T.; Shioiri, T. Total synthesis of vibsanol, a benzofurantype lignani. Tetrahedron Lett., 1999, 40, 4211-4214 (Pubitemid 29294766)
7. Graham, A. E.; McKerrecher, D.; Davies, D. H.; Taylor, R. J. K. Sonogashira coupling reactions of highly oxygenated vinyl halides: The first synthesis of harveynone and epi-harveynone. Tetrahedron Lett., 1996, 37, 7445-7448. (Pubitemid 26326350)
8. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. The chemistry of enediynes, enyne allenes and related compounds. Tetrahedron, 1996, 52, 6453-6518. (Pubitemid 26130448)
9. Wu, R.; Schumm, J. S.; Pearson, D. L.; Tour, J. M. Convergent Synthetic Routes to Orthogonally Fused Conjugated Oligomers Directed toward Molecular Scale Electronic Device Applications. J. Org. Chem., 1996, 61, 6906-6921. (Pubitemid 126528109)
10. Ihle, N. C.; Heathcock, C. H. Palladium-catalyzed intramolecular alkyne-carbon monoxidealkene insertion cascade for synthesis of .alpha.-methylenecyclopentenones. J. Org. Chem., 1993, 58, 560-563
11. Larock, R. C.; Doty, M. J.; Cacchi, S. Synthesis of indenones via palladium-catalyzed annulation of internal alkynes. J. Org. Chem., 1993, 58, 4579-4583.
12. Arcadi, A.; Cacchi, S.; Mainelli, F. Palladium-catalysed coupling of aryl and vinyl triflates or halides with 2-ethynylaniline: An efficient route to functionalized 2-substituted indoles. Tetrahedron Lett., 1989, 30, 2581-2584
13. Roesch, K. R.; Larock, R. C. Synthesis of Isoquinolines and Pyridines via Palladium-Catalyzed Iminoannulation of Internal Acetylenes. J. Org. Chem., 1998, 63, 5306-5307 (Pubitemid 128500809)
14. Larock, R. C.; Yum, E. K.; Refvik, M. D. Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes. J. Org. Chem., 1998, 63, 76527662
15. Larock, R.; Can, X. Palladium-Catalyzed Cross-Coupling of 2,3-Cyclohexadienyl-Substituted Aryl or Vinylic Iodides and Carbon or Heteroatom Nucleophiles. J. Org. Chem., 1999, 64, 1875-1887 (Pubitemid 29152732)
16. Alonso, F.; Belestkaya, I. P.; Yus, M. Transition-Metal-Catalyzed Addition of Heteroatom.Hydrogen Bonds to Alkynes. Chem. Rev., 2004, 104, 3079-3159.
17. Freeman, C. G.; Turner, J. V.; Ward, A. D. The synthesis and preliminary biological testing of some bicyclic guanidine derivatives. Aust. J. Chem., 1978, 31, 179-186.
18. Trapani, G.; Franco, M.; Latrofa, A. Q.; Genchi, G.; Iacobazzi, V.; Ghiani, C. A.; Maciocco, E.; Liso, G. Synthesis and benzodiazepine receptor binding of some imidazo,-pyrimido[2,1-b]benzoxazoles and pyrimido[1,2-a] benzimidazoles. Eur. J. Med. Chem., 1997, 32, 83-89. (Pubitemid 27056086)
19. Saczewski, J.; Brzozowski, Z.; Gdaniec, M. Synthesis of 2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-ones by the domino Michael addition retro-ene reaction of 2-alkoxyiminoimidazolidines and acetylene carboxylates. Tetrahedron, 2005, 61, 5303-5309. (Pubitemid 40693258)
20. Bakherad, M.; Isfahani, H. N.; Keivanloo, A.; Doostmohammadi, N. Pd-Cu catalyzed heterocyclization during Sonogashira coupling: synthesis of 2-benzylimidazo[1,2-a]pyridine. Tetrahedron Lett., 2008, 49, 3819-3822
21. Bakherad, M.; Isfahani, H. N.; Keivanloo, A.; Sang, G. Synthesis of 2-benzylimidazo[2,1-b][1,3]benzothiazoles through palladiumcatalyzed heteroannulation of acetylenic compounds. Tetrahedron Lett., 2008, 49, 6188-6191
22. Kamali,T. A.; Bakherad, M.; Nasrollahzadeh, M.; Farhangi, S.; Habibi, D. Synthesis of 6-substituted imidazo[2,1-b]thiazoles via Pd/Cu-mediated Sonogashira coupling in water. Tetrahedron Lett., 2009, 50, 5459-5462.
23. Sonogashira, K.; Tohda, Y.; Hagihara, N. A convenient synthesis of acetylenes: catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes and bromopyridines. Tetrahedron Lett., 1975, 16, 4467-4470.
24. Theron, F; Verry, M ; Vessiere, R. Rearrangement involving acetylenes. In the chemistry of the carbon-carbon triple bond, Wiley & Sons: Chichester, 1978.