A facile access for the synthesis of some C-2 substituted imidazopyrazines by utilizing the palladium catalyzed Suzuki cross-coupling reaction under microwave irradiation
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关键词:
- Imidazopyrazine
- / Boronic acid
- / Suzuki coupling
- / Microwave
English
A facile access for the synthesis of some C-2 substituted imidazopyrazines by utilizing the palladium catalyzed Suzuki cross-coupling reaction under microwave irradiation
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Key words:
- Imidazopyrazine
- / Boronic acid
- / Suzuki coupling
- / Microwave
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[5](a) C.O. Kappe, D. Dallinger, Controlled microwave heating in modern organic synthesis, Mol. Divers. 13(2009) 71-193;(b) E.N. Koini, N. Avlonitis, E.S. Martins-Durate, et al., Divergent synthesis of 2,6-diaryl-substituted 5,7,8-trimethyl-1,4-benzoxazines via microwave-promoted palladium-catalyzed Suzuki-Miyaura cross coupling and biological evaluation, Tetrahedron 68(2012) 10302-10309;(c) C.O. Kappe, Controlled microwave heating in modern organic synthesis, Angew. Chem. Int. Ed. 43(2004) 6250-6284.[5](a) C.O. Kappe, D. Dallinger, Controlled microwave heating in modern organic synthesis, Mol. Divers. 13(2009) 71-193;(b) E.N. Koini, N. Avlonitis, E.S. Martins-Durate, et al., Divergent synthesis of 2,6-diaryl-substituted 5,7,8-trimethyl-1,4-benzoxazines via microwave-promoted palladium-catalyzed Suzuki-Miyaura cross coupling and biological evaluation, Tetrahedron 68(2012) 10302-10309;(c) C.O. Kappe, Controlled microwave heating in modern organic synthesis, Angew. Chem. Int. Ed. 43(2004) 6250-6284.
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[6](a) A.M. Sajith, K.K. Abdul Khader, N. Joshi, et al., Design, synthesis and structureactivity relationship(SAR) studies of imidazo[4,5-b] pyridine derived purine isosteres and their potential as cytotoxic agents, Eur. J. Med. Chem. 89(2015) 21-31;(b) A. Chandrashekar, B. Eshwarappa, Y.D. Bodke, et al., Synthesis and evaluation of antioxidant properties of novel 1,2,4-triazole-based Schiff base heterocycles, Arch. Pharm. Chem. Life Sci. 346(2013) 922-930;(c) R. Kenchappa, Y.D. Bodke, S.K. Peethambar, S. Telkar, V.K. Bhovi, Synthesis of b-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity, Med. Chem. Res. 22(2013) 4787-4797.[6](a) A.M. Sajith, K.K. Abdul Khader, N. Joshi, et al., Design, synthesis and structureactivity relationship(SAR) studies of imidazo[4,5-b] pyridine derived purine isosteres and their potential as cytotoxic agents, Eur. J. Med. Chem. 89(2015) 21-31;(b) A. Chandrashekar, B. Eshwarappa, Y.D. Bodke, et al., Synthesis and evaluation of antioxidant properties of novel 1,2,4-triazole-based Schiff base heterocycles, Arch. Pharm. Chem. Life Sci. 346(2013) 922-930;(c) R. Kenchappa, Y.D. Bodke, S.K. Peethambar, S. Telkar, V.K. Bhovi, Synthesis of b-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity, Med. Chem. Res. 22(2013) 4787-4797.
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[7](a) K.K. Abdul Khader, A.M. Sajith, M.S.A. Padusha, H.P. Nagaswarupa, A. Muralidharan, Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C-N bond forming reactions with enolizable heterocycles under microwave enhanced conditions, New J. Chem. 38(2014) 1294-1305;(b) K.K. Abdul Khader, A.M. Sajith, M.S.A. Padusha, H.P. Nagaswarupa, A. Muralidharan, Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C-N bond forming reactions with enolizable heterocycles, Tetrahedron Lett. 55(2014) 1778-1783;(c) M.N. Joy, Y.D. Bodke, K.K. Abdul Khader, A.M. Sajith, A rapid approach for the copper, amine and ligand-free Sonogashira coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation, Tetrahedron Lett. 55(2014) 2355-2361;(d) A.M. Sajith, A. Muralidharan, Exploration of copper and amine-free Sonogashira cross coupling reactions of 2-halo-3-alkyl imidazo[4,5-b]pyridines using tetrabutyl ammonium acetate as an activator under microwave enhanced conditions, Tetrahedron Lett. 53(2012) 5206-5210;(e) M.N. Joy, Y.D. Bodke, K.K. Abdul Khader, et al., A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation, RSC Adv. 4(2014) 19766-19777.[7](a) K.K. Abdul Khader, A.M. Sajith, M.S.A. Padusha, H.P. Nagaswarupa, A. Muralidharan, Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C-N bond forming reactions with enolizable heterocycles under microwave enhanced conditions, New J. Chem. 38(2014) 1294-1305;(b) K.K. Abdul Khader, A.M. Sajith, M.S.A. Padusha, H.P. Nagaswarupa, A. Muralidharan, Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C-N bond forming reactions with enolizable heterocycles, Tetrahedron Lett. 55(2014) 1778-1783;(c) M.N. Joy, Y.D. Bodke, K.K. Abdul Khader, A.M. Sajith, A rapid approach for the copper, amine and ligand-free Sonogashira coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation, Tetrahedron Lett. 55(2014) 2355-2361;(d) A.M. Sajith, A. Muralidharan, Exploration of copper and amine-free Sonogashira cross coupling reactions of 2-halo-3-alkyl imidazo[4,5-b]pyridines using tetrabutyl ammonium acetate as an activator under microwave enhanced conditions, Tetrahedron Lett. 53(2012) 5206-5210;(e) M.N. Joy, Y.D. Bodke, K.K. Abdul Khader, et al., A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation, RSC Adv. 4(2014) 19766-19777.
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[8](a) O.O. Navarro, H. Kaur, P. Mahjoor, S.P. Nolan, Cross-coupling and dehalogenation reactions catalyzed by(N-heterocyclic carbene)Pd(allyl)Cl complexes, J. Org. Chem. 69(2004) 3173-3180;(b) J. Moon, S. Lee, Palladium catalyzed-dehalogenation of aryl chlorides and bromides using phosphate ligands, J. Organomet. Chem. 694(2004) 473-477.[8](a) O.O. Navarro, H. Kaur, P. Mahjoor, S.P. Nolan, Cross-coupling and dehalogenation reactions catalyzed by(N-heterocyclic carbene)Pd(allyl)Cl complexes, J. Org. Chem. 69(2004) 3173-3180;(b) J. Moon, S. Lee, Palladium catalyzed-dehalogenation of aryl chlorides and bromides using phosphate ligands, J. Organomet. Chem. 694(2004) 473-477.
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[9](a) A.S. Guram, X. Wang, E.E. Bunel, et al., New catalysts for Suzuki-miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides, J. Org. Chem. 72(2007) 5104-5112;(b) V.F. Slagt, A.H.V. Vries, J.G. Vries, R.M. Kellogg, Practical aspects of carbon-carbon cross-coupling reactions using heteroarenes, Org. Proc. Res. Dev. 14(2010) 30-47;(c) A.M. Sajith, A. Muralidharan, Microwave enhanced Suzuki coupling:a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines, Tetrahedron Lett. 53(2012) 1036-1041.[9](a) A.S. Guram, X. Wang, E.E. Bunel, et al., New catalysts for Suzuki-miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides, J. Org. Chem. 72(2007) 5104-5112;(b) V.F. Slagt, A.H.V. Vries, J.G. Vries, R.M. Kellogg, Practical aspects of carbon-carbon cross-coupling reactions using heteroarenes, Org. Proc. Res. Dev. 14(2010) 30-47;(c) A.M. Sajith, A. Muralidharan, Microwave enhanced Suzuki coupling:a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines, Tetrahedron Lett. 53(2012) 1036-1041.
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