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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 12
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Articles

Triethylamine-catalyzed unprecedented synthesis of 2-amino-4-phenylbenzo [4, 5] imidazo [1,2-a] pyrimidine-3-carbonitrile under solvent free condition

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Pages 1913-1922 | Received 26 Jan 2021, Published online: 12 May 2021

References

  • (a) Ryu, C. K.; Park, R. E.; Ma, M. Y.; Nho, J. H. Bioorg. Med. Chem. Lett. 2007, 17, 2577. (b) Li, J.; Zhao, Y.-F.; Yuan, X.-Y.; Xu, J.-X.; Gong, P. Molecules 2006, 11, 574–582. DOI: 10.3390/11070574. (c) Sinkkonen, J.; Ovcharenko, V.; Zelenin, K. N.; Bezhan, I. P.; Chakchir, B. A.; Al- Assar, F.; Pihlaja, K. Eur. J. Org. Chem. 2002, 2002, 2046. DOI: 10.1002/1099-0690(200207)2002:13<2046::AID-EJOC2046>3.0.CO;2-C. (d) Hoepping, A.; Diekers, M.; Deuther-Conrad, W.; Scheunemann, M.; Fischer, S.; Hiller, A.; Wegner, F.; Steinbach, J.; Brust, P. Bioorg. Med. Chem. 2008, 16, 1184–1194. DOI: 10.1016/j.bmc.2007.10.079.
  • Asobo, P. F.; Wahe, H.; Mbafor, J. T.; Nkengfack, A. E.; Fomum, Z. T.; Sopbue, E. F.; D€Opp, D. J. Chem. Soc. Perkin Trans. 2001, 1, 457–461.
  • Klutchko, S. R.; Hamby, J. M.; Boschelli, D. H.; Wu, Z.; Kraker, A. J.; Amar, A. M.; Hartl, B. G.; Shen, C.; Klohs, W. D.; Steinkampf, R. W. J. Med. Chem. 1998, 413276–3292.
  • Alajarin, R.; Vaquero, J. J.; Alvarez-Builla, J.; de Casa-Juana, M. F.; Sunkel, C.; Priego, J. G.; Gomez-Sal, P.; Torres, R. Bioorg. Med. Chem. 1994, 2, 323–329. DOI: 10.1016/s0968-0896(00)82188-4.
  • Badawey, E.; Kappe, T. Eur. J. Med. Chem. 1995, 30, 327–332. DOI: 10.1016/0223-5234(96)88241-9.
  • Le Corre, L.; Girard, A.-L.; Aubertin, J.; Radvanyi, F.; Benoist-Lasselin, C.; Jonquoy, A.; Mugniery, E.; Legeai-Mallet, L.; Busca, P.; Le Merrer, Y. Org. Biomol. Chem. 2010, 8, 2164–2173. DOI: 10.1039/b923882d.
  • Neochoritis, C. G.; Zarganes-Tzitzikas, T.; Tsoleridis, C. A.; Stephanidou Stephanatou, J.; Kontogiorgis, C. A.; Hadjipavlou-Litina, D. J.; Choli-Papadopoulou, T. Eur. J. Med. Chem. 2011, 46, 297–306. DOI: 10.1016/j.ejmech.2010.11.018.
  • (a) Veeranarayana Reddy, M.; Dindulkar, S. D.; Jeong, Y. T. Tetrahedron Lett. 2011, 52, 4764–4767. DOI: 10.1016/j.tetlet.2011.07.027. (b) Yadav, N.; Kamil Hussain, M.; Imran Ansari, M.; Gupta, P. K.; Hajel, K. RSC Adv. 2013, 3, 540–544. DOI: 10.1039/C2RA22355D.
  • (a) Eskandar, K.; Nadiya, K.; Ozra, A. Tetrahedron 2014, 70, 1383. (b) Ghaffari Khaligh, N. RSC Adv. 2013, 3, 99–110. DOI: 10.1039/C2RA21295A. (c) Shankar Singh, M.; Chowdhury, S. RSC Adv. 2012, 2, 4547. DOI: 10.1039/c2ra01056a. (d) Veeranarayana Reddy, M.; Jeong, Y. T. Synlett 2012, 2012, 2985. (e) Mulla, S. A. R.; Pathan, M. Y.; Chavan, S. S.; Gample, S. P.; Sarkar, D. RSC Adv. 2014, 4, 7666. DOI: 10.1039/c3ra45853a.
  • (a) Kumar, A.; Gupta, M. K.; Kumar, M.; Saxena, D. RSC Adv. 2013, 3, 1673–1678. DOI: 10.1039/C2RA22428C. (b) Bhaskar Kumar, T.; Sumanth, C.; Dhanunjaya Rao, A. V.; Dipak, K.; Srinivasa Rao, M.; Chandra Sekhar, K. B.; Shiva Kumar, K.; Pal, M. RSC Adv. 2012, 2, 11510. DOI: 10.1039/c2ra22302c.
  • (a) Nandi, G. C.; Samai, S.; Singh, M. S. Synlett 2010, 2010, 1133–1137. DOI: 10.1055/s-0029-1219574. (b) Verma, R. K.; Verma, G. K.; Shukla, G.; Singh, M. S. RSC Adv. 2012, 2, 2413–2421. DOI: 10.1039/c2ra00987k. (c) Chua, S.; Alni, A.; Jocelyn Chan, L.; Yamane, M.; Loh, T. Tetrahedron 2011, 67, 5079–5082. DOI: 10.1016/j.tet.2011.04.101.
  • Yao, C. S.; Lei, S.; Wang, C. H.; Yu, C. X.; Shao, Q. Q.; Tu, S. J. Chin. J. Chem. 2008, 26, 2107–2111. DOI: 10.1002/cjoc.200890376.
  • Meshram, H. M.; Kumar, A. S.; Kumar, G. S.; Swetha, A.; Reddy, B. C.; Ramesh, P. Der Pharma Chem. 2012, 4, 956–960.
  • Warekar, P. P.; Patil, P. T.; Patil, K. T.; Jamale, D. K.; Kolekar, G. B.; Anbhule, P. V. Synth. Commun. 2016, 46, 2022–2030. DOI: 10.1080/00397911.2016.1244273.
  • Wu, L.; Yan, F.; Yang, C. Bull. Chem. Soc. Ethiop. 2010, 24, 417–423.
  • Shang, X.; Geng, M.; Wu, L. Asian J. Chem. 2012, 24, 515–517.
  • (a) Nunes, J. J.; Zhu, X. T.; Amouzegh, P.; Ghiron, C.; Johnston, D. N.; Power, E. C. WO. Pat. 2005, 2005009443. (b) Fu, R.-G.; You, Q.-D.; Yang, L.; Wu, W.-T.; Jiang, C.; Xu, X.-L. Bioorg. Med. Chem. 2010, 18, 8035–8043. DOI: 10.1016/j.bmc.2010.09.020. (c) Zanatta, N.; Amaral, S. S.; Esteves-Souza, A.; Echevarria, A.; Brondani, P. B.; Flores, D. C.; Bonacorso, H. G.; Flores, A. F. C.; Martins, M. A. P. Synthesis 2006, 2006, 2305–2312. DOI: 10.1055/s-2006-942444. (d) Gong, H.; Qi, H.; Sun, W.; Zhang, Y.; Jiang, D.; Xiao, J.; Yang, X.; Wang, Y.; Li, S. Molecules 2012, 17, 9961–9970. DOI: 10.3390/molecules17089961.
  • Hemmati, B.; Javanshir, S.; Dolatkhah, Z. RSC Adv. 2016, 6, 50431–50436.
  • Shirini, F.; Seddighi, M.; Goli-Jolodar, O. J. Iran. Chem. Soc. 2016, 13, 2013–2018. DOI: 10.1007/s13738-016-0918-7.
  • Abedini, M.; Shirini, F.; Mousapour, M.; Jolodar, O. G. Res. Chem. Intermed. 2016, 42, 6221–6229. DOI: 10.1007/s11164-016-2456-4.
  • Shaabani, A.; Rahmati, A.; Naderi, S. Bioorg. Med. Chem. Lett. 2005, 15, 5553–5557. DOI: 10.1016/j.bmcl.2005.08.101.
  • Hu, L.; Zhan, Z.; Lei, M.; Hu, L. J. Chem. Res. (S) 2012, 36, 738–739. DOI: 10.3184/174751912X13528011362074.
  • Shaterian, H. R.; Fahimi, N.; Azizi, K. Res. Chem. Intermed. 2014, 40, 1879–1898. DOI: 10.1007/s11164-013-1087-2.
  • Tu, S.; Shao, Q.; Zhou, D.; Cao, L.; Shi, F.; Li, C. J. Heterocycl. Chem. 2007, 44, 1401–1406. DOI: 10.1002/jhet.5570440625.
  • Liu, J.; Lei, M.; Hu, L. Green Chem. 2012, 14, 2534. DOI: 10.1039/c2gc35745c.
  • Reddy, M. V.; Kim, J. S.; Lim, K. T.; Jeong, Y. T. Tetrahedron Lett. 2014, 55, 6459–6462. DOI: 10.1016/j.tetlet.2014.09.135.
  • (a) Jeong, Y. T.; Balwe, S. G. Org. Chem. Front. 2018, 5, 1628–1632. DOI: 10.1039/C8QO00071A. (b) Balwe, S. G.; Jeong, Y. T. RSC Adv. 2016, 6, 107225–107232. DOI: 10.1039/C6RA24183B. (c) Jadhav, A. M.; Balwe, S. G.; Lim, K. T.; Jeong, Y. T. Tetrahedron 2017, 73, 2806–2813. DOI: 10.1016/j.tet.2017.03.084. (d) Jadhav, A. M.; Kim, Y. I.; Lim, K. T.; Jeong, Y. T. Tetrahedron Lett. 2018, 59, 554–557. DOI: 10.1016/j.tetlet.2018.01.008. (e) Yadav, M. B.; Balwe, S. G.; Kim, J. T.; Cho, B. G.; Jeong, Y. T. Synth. Commun. 2020, 50, 1456–1467. DOI: 10.1080/00397911.2020.1737129. (f) Yadav, M. B.; Vagh, S. S.; Jeong, Y. T. Res. Chem. Intermed. 2020, 46, 3801–3815. DOI: 10.1007/s11164-020-04173-0.
  • Li, L.; Xu, H.; Dai, L.; Xi, J.; Gao, L.; Rong, L. Tetrahedron 2017, 73, 5358–5365. DOI: 10.1016/j.tet.2017.07.035.

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