Effective Suzuki-Miyaura arylation and sonogashira aryl alkynylation on N-heteroaromatic cations: Synthesis of substituted pyridine-fused cationic heterocycles

Synthesis

Volumn , Issue 18, 2011, Pages 3006-3014

  Paira, Rupankar ^a   Sahu, Krishnendu B ^a   Mondal, Shyamal ^a   Maity, Arindam ^a   Hazra, Abhijit ^a   Naskar, Subhendu ^a   Saha, Pritam ^a   Padmanaban, E ^a   Banerjee, Sukdeb ^a   Mondal, Nirup B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

cross coupling; diazepanium; diazocanium; fused rings; Sonogashira; Suzuki Miyaura

Indexed keywords

CROSS-COUPLINGS; DIAZEPANIUM; DIAZOCANIUM; FUSED RING; SONOGASHIRA; SUZUKI-MIYAURA;

MICROWAVE IRRADIATION;

SYNTHESIS (CHEMICAL);

ALUMINUM OXIDE; AROMATIC COMPOUND; CATION; CHEMICAL COMPOUND; DIAZAPANIUM DERIVATIVE; DIAZOCANIUM DERIVATIVE; HETEROCYCLIC COMPOUND; POLYCYCLIC TETRAHYDROPYRIMIDINIUM; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; MICROWAVE IRRADIATION; SONOGASHIRA REACTION; STRUCTURE ANALYSIS; SUZUKI MIYAURA ARYLATION; SYNTHESIS;

EID: 80052648969     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1261033     Document Type: Article

References (29)

1. Brana M F., Cacho M, Gradillas A, dePascual-Teresa B, Ramos A, Curr. Pharm. Des. 2001 7 1745
2. Galietta L J. V., Springsteel M F., Eda M, Niedzinski E J., By K, Haddadin M J., Kurth M J., Nantz M H., Verkman A S., J. Biol. Chem. 2001 276 19723
3. Martínez V, Burgos C, Alvarez-Builla J, Fernández G, Domingo A, García-Nieto R, Gago F, Manzanares I, Cuevas C, Vaquero J J., J. Med. Chem. 2004 47 1136
4. Howarth J, Hanlon K, Tetrahedron Lett. 2001 42 751
5. Howarth J, Hanlon K, Bioorg. Med. Chem. Lett. 2003 13 2017
6. García D, Cuadro A M., Alvarez-Builla J, Vaquero J J., Org. Lett. 2004 6 4175
7. Lambert C, Gaschler W, Nöll G, Weber M, Schmälzlin E, Bräuchle C, Meerholz K, J. Chem. Soc., Perkin Trans. 2 2001 964
8. Barchín B M., Valenciano J, Cuadro A M., Alvarez-Builla J, Vaquero J J., Org. Lett. 1999 1 545
9. Reyes M J., Izquierdo M L., Alvarez-Builla J, Tetrahedron Lett. 2004 45 8713
10. Córdoba M, Izquierdo M L., Alvarez-Builla J, Tetrahedron Lett. 2011 52 1738
11. Bringmann G, Gunther C, Ochse M, Schupp O, Tasler S, In Progress in the Chemistry of Organic Natural Products Vol. 82 Herz W Falk H Kirby G W. Moore R E. Tamm C Springer Vienna 2001 1-249
12. Bringmann G, Feineis D, Acta Chim. Ther. 2000 26 151
13. Bringmann G, In Guidelines and Issues for the Discovery and Drug Development against Tropical Diseases Vial H Fairlamb A Ridley R World Health Organisation Geneva 2003 145-152
14. Miyaura N, Yamada K, Suzuki A, Tetrahedron Lett. 1979 3437
15. Miyaura N, Suzuki A, Chem. Rev. 1995 95 2457
16. Suzuki A, J. Organomet. Chem. 1999 576 147
17. Suzuki A, J. Organomet. Chem. 2002 653 83
18. Kotha S, Lahiri K, Kashinath D, Tetrahedron 2002 58 9633
19. Miyaura N, In Metal-Catalyzed Cross-Coupling Reactions 2nd ed., Vol. 1 deMeijere A Diederich F Wiley-VCH Weinheim 2004 41-124
20. DeClercq E, Descamps J, Balzarini J, Giziewicz J, Barr P J., Robins M J., J. Med. Chem. 1983 26 661
21. Fairlamb I J. S., Marrison L R., Dickinson J M., Lu F J., Schmidt J P., Bioorg. Med. Chem. 2004 12 4285
22. Sonogashira K, Tohda Y, Hagihara N, Tetrahedron Lett. 1975 4467
23. Sonogashira K, Yatake T, Tohda Y, Takahashi S, Hagihara N, Chem. Commun. 1977 291
24. Saha P, Naskar S, Paira P, Hazra A, Sahu K B., Paira R, Banerjee S, Mondal N B., Green Chem. 2009 7 931
25. Sahu K B., Hazra A, Paira P, Saha P, Naskar S, Paira R, Banerjee S, Sahu N P., Mondal N B., Luger P, Weber M, Tetrahedron 2009 65 6941
26. Paira P, Paira R, Hazra A, Sahu K B., Naskar S, Saha P, Mondal S, Maity A, Banerjee S, Mondal N B., Tetrahedron Lett. 2009 50 5505
27. Paira R, Maity A, Naskar S, Mondal S, Paira P, Hazra A, Sahu K B., Saha P, Banerjee S, Mondal N B., Synthesis 2010 3520
28. Paira R, Maity A, Mondal S, Naskar S, Sahu K B., Saha P, Hazra A, Padmanaban E, Banerjee S, Mondal N B., Tetrahedron Lett. 2011 52 1653
29. Cheng D, Croft l, Abdi M, Lightfoot A, Gallagher T, Org. Lett. 2007 9 5175