JOURNAL BROWSE
Search
Advanced SearchSearch Tips
Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP
facebook(new window)  Pirnt(new window) E-mail(new window) Excel Download
 Title & Authors
Cross-Coupling Reaction of 2-halo1-methyl-1H-imidazo[4,5-b]pyridine Offers a New Synthetic Route to Mutagenic Heterocyclic Amine-PHIP and DMIP
Sajith, Ayyiliath M.; Muralidharan, Arayambath; Karuvalam, Ranjith P.; Haridas, Karickal R.;
  PDF(new window)
 Abstract
A modified synthetic approach to the synthesis of heterocyclic food mutagens, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PHIP) and 2-amino-1,6-dimethylimidazo[4,5-b]pyridine (DMIP) is reported. This route highlights an optimized palladium catalysed Buchwald cross-coupling of 2-halo-1-methyl-imidazo[4,5-b]pyridine with benzophenoneimine followed by acidic hydrolysis to yield compound 7. Using finely tailored conditions, Suzuki cross-coupling reactions with highly efficient catalytic systems were performed as the final step on 8 to introduce the aryl group and methyl group on the heterocyclic core.
 Keywords
Buchwald coupling;Imidazopyridine;Suzuki coupling;Heterocyclic amines;
 Language
English
 Cited by
1.
Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C–N bond forming reactions with enolizable heterocycles, Tetrahedron Letters, 2014, 55, 10, 1778  crossref(new windwow)
2.
Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition, Australian Journal of Chemistry, 2017, 70, 1, 44  crossref(new windwow)
3.
Facile Synthesis of Fully Decorated Imidazo[4,5-b] and Imidazo[4,5-c] Pyridines in Aqueous DMF via C-H Activation under Microwave Irradiation, ChemistrySelect, 2016, 1, 10, 2265  crossref(new windwow)
4.
A Highly Efficient Catalyst for the Suzuki Cross-coupling Reaction of 3-Chloro-5-oxadiazol-2-yl Pyridine, Journal of Heterocyclic Chemistry, 2015, 52, 6, 1748  crossref(new windwow)
5.
Synthesis, Spectral Characterization, and Antimicrobial Activity of Novel 2,4,6-Trisubstituted Quinazoline Derivatives by Buchwald and Suzuki Coupling Reactions, Journal of Heterocyclic Chemistry, 2016, 53, 5, 1528  crossref(new windwow)
6.
Palladium-Catalyzed Suzuki Cross-Coupling of 2-Halo-Deazapurines with Potassium Organotrifluoroborate Salts in the Regioselective Synthesis of Imidazo[4,5-b]pyridine Analogues, Australian Journal of Chemistry, 2016, 69, 6, 618  crossref(new windwow)
7.
NMI/MsCl-Mediated Amide Bond Formation of Aminopyrazines and Aryl/Heteroaryl Carboxylic Acids: Synthesis of Biologically Relevant Pyrazine Carboxamides., ChemistrySelect, 2017, 2, 25, 7706  crossref(new windwow)
 References
1.
Aridoss, G.; Balasubramaniam, S.; Parthiban, P.; Kabilan, S. Eur. J. Med. Chem. 2006, 41, 268. crossref(new window)

2.
Youssef, A. F.; E1-Gendy, M. A.; Aboutaleb, N. A. E.; Ahmed, S. H. Egypt. J. Pharm. Sci. 1982, 23, 131.

3.
Cristalli, G.; Vittori, S.; Eleuteri, A.; Volpini, R.; Vamaioni, E.; Lupidi, G.; Mohmoud, N.; Bevilacqua, F.; Palu, G. J. Med. Chem. 1995, 38, 4019. crossref(new window)

4.
Temple, C.; Rose, J. D.; Combu, R. N.; Rener, G. A. J. Med. Chem. 1987, 30, 1746. crossref(new window)

5.
Temple, C. J. Med. Chem. 1990, 33, 656. crossref(new window)

6.
Bukowski, L.; Janowiec, M. Pharmazie 1989, 44, 267.

7.
Itoh, T.; Mase, T. Tetrahedron Lett. 2005, 46, 3573. crossref(new window)

8.
Sajith, A. M.; Muralidharan, A. Tetrahedron Lett. 2012, 53, 1036. crossref(new window)

9.
Doucet, H.; Hierso, J. Angew. Chem., Int. Ed. 2007, 46, 834. crossref(new window)

10.
Felton, J. S.; Knize, M. G.; Shen, N. H.; Lewis, I. R.; Anderson, B. D.; Happe, J.; Hatch, F. T. Carcinogenesis 1986, 7, 1081. crossref(new window)

11.
Buonarati, N. H.; Tucker, J. V.; Minkler, J. L.; Wu, R. W.; Thompson, L. H.; Felton, J. S. Mutagenesis 1991, 6, 253-259. crossref(new window)

12.
Bentiss, F.; Lagrenee, M.; Barby, D. Tetrahedron Lett. 2000, 41, 1539. crossref(new window)

13.
Besson, T.; Guil-lard, J.; Rees, C. W. Tetrahedron Lett. 2000, 41, 1027. crossref(new window)

14.
Ranu, B. C.; Hajra, A.; Jana, U. C. Tetrahedron Lett. 2000, 41, 5891. crossref(new window)

15.
Knize, M. G.; Felton, J. S. Heterocycles 1986, 24, 1815-1819. crossref(new window)

16.
Fabio, S. B.; Tullio, C. Tetrahedron Lett. 1997, 38, 7793-7796. crossref(new window)

17.
Christopher, J. C.; James, E. B.; Mary, J. T. ARKIVOC 2002, 90-96.

18.
Tominari, C.; Akiko, T.; Haruyuki, Y.; Kenichi, H.; Eiichi, S.; SatoshI, H. J. Org. Chem. 1993, 58, 7952-7954. crossref(new window)

19.
Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367-6370. crossref(new window)

20.
Lee, S.; Jorgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729-2732. crossref(new window)

21.
Huang, X. H.; Buchwald, S. L. Org. Lett. 2001, 3, 3417-3419. crossref(new window)