Synthesis of quinoxalines through iodine-catalyzed one-pot annulation of alkynes with o-phenylenediamines

References

• For selected reviews, see: (a) Guo, X.-X.; Gu, D.-W.; Wu, Z.; Zhang, W. Chem. Rev. 2015, 115, 1622; (b) Eftekhari-Sis, B.; Zirak, M. Chem. Rev. 2015, 115, 151; (c) Yamamoto, Y. Chem. Soc. Rev. 2014, 43, 1575; (d) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084; (e) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Rev. 2013, 113, 1; (f) Patil, N. T.; Yamamoto, Y. Chem. Rev. 2008, 108, 3395; (g) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
   PubMed Web of Science ®Google Scholar
• (a) Diana, P.; Martorana, A.; Barraja, P.; Montalbano, A.; Dattolo, G.; Cirrincione, G.; Dall’Acqua, F.; Salvador, A.; Vedaldi, D.; Basso, G.; et al. J. Med. Chem. 2008, 51, 2387; (b) Zarranz, B.; Jaso, A.; Aldana, I.; Monge, A. Bioorg. Med. Chem. 2004, 12, 3711.
   PubMed Web of Science ®Google Scholar
• (a) Morales-Castellanos, J. J.; Ramírez-Hernández, K.; Gómez-Flores, N. S.; Rodas-Suárez, O. R.; Peralta-Cruz, J. Molecules 2012, 17, 5164; (b) Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604.
   PubMed Web of Science ®Google Scholar
• Burguete, A.; Pontiki, E.; Hadjipavlou-Litina, D.; Villar, R.; Vicente, E.; Solano, B.; Ancizu, S.; Pérez-Silanes, S.; Aldana, I.; Monge, A. Bioorg. Med. Chem. Lett. 2007, 17, 6439.
   PubMed Web of Science ®Google Scholar
• Rong, F.; Chow, S.; Yan, S.; Larson, G.; Hong, Z.; Wu, J. Bioorg. Med. Chem. Lett. 2007, 17, 1663.
   PubMed Web of Science ®Google Scholar
• (a) Myers, M. R.; He, W.; Hanney, B.; Setzer, N.; Maguire, M. P.; Zulli, A.; Bilder, G.; Galzcinski, H.; Amin, D.; Needle, S.; Spada, A. P. Bioorg. Med. Chem. Lett. 2003, 13, 3091; (b) Gazit, A.; App, H.; McMahon, G.; Chen, J.; Levitzki, A.; Bohmer, F. D. J. Med. Chem. 1996, 39, 2170.
   PubMed Web of Science ®Google Scholar
• For selected examples, see: (a) Jeganathan, M.; Dhakshinamoorthy, A.; Pitchumani, K. Tetrahedron Lett. 2014, 55, 1616; (b) Jeena, V.; Robinson, R. S. Tetrahedron Lett. 2014, 55, 642; (c) Hille, T.; Irrgang, T.; Kempe, R. Chem.-Eur. J. 2014, 20, 5569; (d) Cai, J.-J.; Zou, J.-P.; Pan, X.-Q.; Zhang, W. Tetrahedron Lett. 2008, 49, 7386.
   Web of Science ®Google Scholar
• (a) Zhang, F.; Xi, Y.; Lu, Y.; Wang, L.; Liu, L.; Li, J.; Zhao, Y. Chem. Commun. 2014, 50, 5771; (b) Shi, S.; Wang, T.; Yang, W.; Rudolph, M.; Hashmi, A. S. K. Chem.-Eur. J. 2013, 19, 6576; (c) Sagadevan, A.; Ragupathi, A.; Hwang, K. C. Photochem. Photobiol. Sci. 2013, 12, 2110; (d) Xu, N.; Gu, D.-W.; Dong, Y.-S.; Yi, F.-P.; Cai, L.; Wu, X.-Y.; Guo, X.-X. Tetrahedron Lett. 2015, 56, 1517; (e) Chandrasekhar, S.; Reddy, N. K.; Kumar, V. P. Tetrahedron Lett. 2010, 51, 3623.
   PubMed Web of Science ®Google Scholar
• (a) Hazarika, D.; Phukan, P. Tetrahedron 2017, 73, 1374; (b) Viswanadham, K. K. D. R.; Reddy, M. P.; Sathyanarayana, P.; Ravi, O.; Kant, R.; Bathula, S. R. Chem. Commun. 2014, 50, 13517; (c) Okumura, S.; Takeda, Y.; Kiyokawa, K.; Minakata, S. Chem. Commun. 2013, 49, 9266; (d) Chen, C.-Y.; Hu, W.-P.; Liu, M.-C.; Yan, P.-C.; Wang, J.-J.; Chung, M.-I. Tetrehedron 2013, 69, 9735; (e) Adib, M.; Sheibani, E.; Abbasi, A.; Bijanzadeh, H. R. Tetrahedron Lett. 2007, 48, 1179.
   Web of Science ®Google Scholar
• For the reviews, see: (a) Finkbeiner, P.; Nachtsheim, B. J. Synthesis 2013, 45, 979; (b) Jereb, M.; Vražič, D.; Zupan, M. Tetrahedron 2011, 67, 1355; (c) Mphahlele, M. J. Molecules 2009, 14, 4814.
   Web of Science ®Google Scholar
• For selected examples, see: (a) Wu, X.; Gao, Q.; Liu, S.; Wu, A. Org. Lett. 2014, 16, 2888; (b) Wen, L.-R.; Men, L.-B.; He, T.; Ji, G.-J.; Li, M. Chem.-Eur. J. 2014, 20, 5028; (c) Yang, F.-L.; Tian, S.-K. Angew. Chem. Int. Ed. 2013, 52, 4929 (d) Yan, Y.; Zhang, Y.; Feng, C.; Zha, Z.; Wang, Z. Angew. Chem. Int. Ed. 2012, 51, 8077.
   PubMed Web of Science ®Google Scholar
• Roesch, K. R.; Larock, R. C. J. Org. Chem. 2001, 66, 412.
   PubMed Web of Science ®Google Scholar