Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 1
189
Views
11
CrossRef citations to date
0
Altmetric
ARTICLE

Synthesis of novel coumarinyl-pyrido[2,3-d]pyrimidine-2,4-diones using task-specific magnetic ionic liquid, [AcMIm]FeCl4 as catalyst

, , , , , & show all
Pages 104-111 | Received 07 Jul 2019, Published online: 07 Nov 2019

References

  • (a) Sun, X.; Luo, H.; Dai, S. Chem. Rev. 2012, 112, 2100-2128. DOI: 10.1021/cr200193x.(b) Plechkova, N. V.; Seddon, K. R. Chem. Soc. Rev. 2008, 37, 123-150. DOI: 10.1039/B006677J.
  • (a) D’Anna, F.; Noto, R. Tetrahedron Lett. 2007, 63, 11681-11685. DOI: 10.1016/j.tet.2007.08.116. (b) Astolfi, D. L.; Mayville, F. C. Tetrahedron Lett. 2003, 44, 9223-9224. DOI: 10.1016/j.tetlet.2003.10.036.
  • (a) Sharifi, A.; Hosseini, F.; Ghonouei, N.; Ghonoueia, N.; Abaeea, M. S.; Mirzaeia, M.; Mesbaha, A. W.; Harms, K. J. Sulfur Chem. 2015, 36, 257-269. DOI: 10.1080/17415993.2015.1014483. (b) Jagadalea, S. D.; Deshmukh, M. B.; Mulikb, A. G.; Chandamb, D. R.; Patilb, P. P.; Patilb, D. R.; Sankpal, S. A. Der. Pharma. Chemica. 2012, 4, 202-207.
  • Ardhapure, S. S.; Shinde, P. S.; Shinde, S. S.; Katariya, M. V.; Ingle, R. D.; Vyawahare, S. K.; Ameta, K. L.; Pawar, R. P. Int. J. Chemtech. App. 2012, 1, 60-63.
  • Shinde, P. S.; Shinde, S. S.; Dake, S. A.; Sonekar, V. S.; Deshmukh, S. U.; Thorat, V. V.; Andurkar, N. M.; Pawar, R. P. Arab. J. Chem. 2014, 7, 1013-1016. DOI: 10.1016/j.arabjc.2010.12.028.
  • Mouradzadegun, A.; Najafi, Z.; Elahi, S. J. Sulfur Chem. 2015, 36, 624-629. DOI: 10.1080/17415993.2015.1077388.
  • (a) Hayashi, S.; Hamaguchi, H. Chem. Lett. 2004, 33, 1590-1591. DOI: 10.1246/cl.2004.1590. (b) Lee, S. H.; Ha, S. H.; You, C. Y.; Koo, Y. M. Korean J. Chem. Eng. 2007, 24, 36-437. DOI: 10.1007/s11814-007-0075-x.
  • (a) Bica, K.; Gaertner, P. Eur. J. Org. Chem. 2008, 2008, 3453-3456. DOI: 10.1002/ejoc.200800323. (b) Tang, S.; Babai, A.; Mudring, A. V. Angew. Chem. Int. 2008, 47, 7631-7634. Angew. Chem. 2008, 120, 7743-7746. DOI: 10.1002/ange.200801159. (c) Yoshida, Y.; Saito, G. J. Mater. Chem. 2006, 16, 1254-1262. DOI: 10.1039/b515391c.
  • (a) Bolm, C.; Legros, J.; Paih, J. L.; Zani, L. Chem. Rev. 2004, 104, 6217-6254. DOI: 10.1021/cr040664h. (b) Plietker, B. Iron Catalysis: Fundamentals and Applications: 33 (Topics in Organometallic Chemistry. Springer: Berlin, 2010.
  • (a) Panja, S. K.; Saha, S. RSC Adv. 2013, 3, 14495-14500. DOI: 10.1039/c3ra42039f. (b) Wang, H.; Yan, R.; Li, Z.; Zhang, X.; Zhang, S. Catal. Commun. 2010, 11, 763-767. DOI: 10.1016/j.catcom.2010.02.011. (c) Valkenberg, M. H.; deCastro, C.; Hölderich, W. F. Catal. A: Gen. 2001, 215, 185-190. DOI: 10.1016/S0926-860X(01)00531-2. (d) Bica, K.; Gaertner, P. Org. Lett. 2006, 8, 733-735. DOI: 10.1021/ol052965z. (e) Nguyen, M.; Nguyen, L.; Jeon, E.; Kim, J.; Cheong, M.; Kim, H.; Lee, J. Catal. 2008, 258, 5-13. DOI: 10.1016/j.jcat.2008.05.008.
  • Saha, A.; Payra, S.; Dutta, D.; Banerjee, S. Chem. Plus Chem. 2017, 82, 1129-1134. DOI: 10.1002/cplu.201700221.
  • (a) El-Ashry, S. H.; El-Nemr, A. Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates; Wiley-Blackwell: Oxford, UK, 2005. (b) Smil, D. V.; Manku, S.; Chantigny, Y. A.; Leit, S.; Wahhab, A.; Yan, T. P.; Fournel, M.; Maroun, C.; Li, Z.; Lemieux, A.-M.; et al. Bioorg. Med. Chem. Lett. 2009, 19, 688-692. DOI: 10.1016/j.bmcl.2008.12.045.
  • (a) Mahale, S.; Bharate, S. B.; Manda, S.; Joshi, P.; Bharate, S. S.; Jenkins, P. R.; Vishwakarma, R. A.; Chaudhuri, B. J. Med. Chem. 2014, 57, 9658-9672. DOI: 10.1021/jm5014743. (b) Barvian, M.; Boschelli, D. H.; Cossrow, J.; Dobrusin, E.; Fattaey, A.; Fritsch, A.; Fry, D.; Harvey, P.; Keller, P.; Garrett, M.; et al. J. Med. Chem. 2000, 43, 4606-4616. DOI: 10.1021/jm000271k. (c) Chen, Y.; Wu, S.; Tu, S.; Shi, F.; Li, C. J. Heterocycl. Chem. 2008, 45, 1243-1246. DOI: 10.1002/jhet.5570450452. (d) Chaudhari, P. K. Int. J. Life Sci. Pharma. Res. 2011, 1, 71-76. (e) Piper, J. R.; McCaleb, G. S.; Montgomery, J. A.; Kisliuk, R. L.; Gaumont, Y.; Sirotnak, F. M. J. Med. Chem. 1986, 29, 1080-1087. DOI: 10.1021/jm00156a029. (f) Robins, B. R. K.; Hitchings, G. H. J. Am. Chem. Soc. 1958, 80, 3449. DOI: 10.1021/ja01546a061. (g) Quintela, J. M.; Peinador, C.; Botana, L.; Estevez, M.; Riguera, R. Bioorg. Med. Chem. 1997, 5, 1543 DOI: 10.1016/S0968-0896(97)00108-9. (h) Nam, G.; Yoon, C. M.; Kim, E.; Rhee, C. K.; Kim, J. H.; Shin, J. H.; Kim, S. H. Bioorg. Med. Chem. Lett. 2001, 11, 611. DOI: 10.1016/s0960-894x(00)00681-8. (i) Zhu Zheng, G.; Mao, Y.; Hung Lee, C.; Pratt, J. K.; Koenig, J. R.; Perner, R. J.; Cowart, M. D.; Gfesser, G. A.; McGraughty, S.; Chu. Katharine, L.; et al. Bioorg. Med. Chem. Lett. 2003, 13, 3041DOI: 10.1016/s0960-894x(03)00642-5.
  • (a) Xue, H.; Lu, X.; Zheng, P.; Liu, L.; Han, C.; Hu, J.; Liu, Z.; Ma, T.; Li, Y.; Wang, L.; et al. J. Med. Chem. 2010, 53, 1397-1401. DOI: 10.1021/jm901653e. (b) Devji, T.; Reddy, C.; Woo, C.; Awale, S.; Kadota, S.; Carrico-Moniz, D. Bioorg. Med. Chem. Lett. 2011, 21, 5770-5773. DOI: 10.1016/j.bmcl.2011.08.005. (c) Yeh, J.-Y.; Coumar, M. S.; Horng, J.-T.; Shiao, H.-Y.; Kuo, F.-M.; Lee, H.-L.; Chen, I.-C.; Chang, C.-W.; Tang, W.-F.; Tseng, S.-N.; et al. J. Med. Chem. 2010, 53, 1519-1533. DOI: 10.1021/jm901570x. (d) Anand, P.; Singh, B.; Singh, N. Bioorg. Med. Chem. 2012, 20, 1175-1180. DOI: 10.1016/j.bmc.2011.12.042.
  • Shaabani, A.; Seyyedhamzeh, M.; Maleki, A.; Rezazadeh, F.; Behnam, M. J. Comb. Chem. 2009, 11, 375-377. DOI: 10.1021/cc800189j.
  • Hughes, D. D.; Bagley, M. C. Synlett 2002, 2002, 1332-1334. DOI: 10.1055/s-2002-32953.
  • Lee, T. C.; Salemnick, G. J. Org. Chem. 1975, 40, 3608-3610. DOI: 10.1021/jo00912a035.
  • Shi, D. Q.; Ni, S. N.; Yang, F.; Shi, J. W.; Dou, G. L.; Li, X. Y.; Wang, X. S.; Ji, S. J. J. Heterocycl. Chem. 2008, 45, 693-702. DOI: 10.1002/jhet.5570450310.
  • (a) Sharma, A.; Gudala, S.; Ambati, S. R.; Mahapatra, S. P.; Raza, A.; Aruna, L. V.; Payra, S.; Jha, A.; Kumar, A.; Penta, S.; Banerjee, S. Chem. Select 2018, 3, 11012-11019. DOI: 10.1002/slct.201801414. (b) Penta, S.; Gadidasu, K. K.; Basavoju, S.; Rao, V. R. Tetrahedron Lett. 2013, 54, 5663-5666. DOI: 10.1016/j.tetlet.2013.07.148. (c) Penta, S.; Rao, V. R. J. Sulfur Chem. 2011, 32, 327-333. DOI: 10.1080/17415993.2011.588951. (d) Penjarla, S.; Reddy, A. R.; Banerjee, S.; Penta, S.; Sanghvi, Y. S. Tetrahedron Lett. 2017, 58, 2588-2591. DOI: 10.1016/j.tetlet.2017.05.066. (e) Sharma, A.; Satish, G.; Penta, S. J. Heterocyclic Chem. 2016, 53, 1086-1090. DOI: 10.1002/jhet.2362. (f) Satish, G.; Sharma, A.; Gadidasu, K. K.; Rao, V. R.; Penta, S. Chem. Heterocycl. Comp. 2016, 52, 409-414. DOI: 10.1007/s10593-016-1902-y. (g) Penta, S.; Rao, V. R. Synth. Commun. 2012, 42, 3395-3402. DOI: 10.1080/00397911.2011.558969. (h) Penta, S.; Chunduru, V. S. R.; Rao, V. R. Chem. Heterocycl. Comp. 2011, 47, 448-451. DOI: 10.1007/s10593-011-0779-z. (i) Penta, S.; Rao, V. R. J. Heterocyclic Chem. 2013, 50, 859-862. DOI: 10.1002/jhet.1589.
  • (a) Saha, A.; Payra, S.; Verma, S. K.; Mandal, M.; Thareja, S.; Banerjee, S. RSC Adv. 2015, 5, 100978-100983. DOI: 10.1039/C5RA16643H. (b) Ranu, B. C.; Saha, A.; Banerjee, S. Eur. J. Org. Chem. 2008, 2008, 519-523. DOI: 10.1002/ejoc.200700842. (c) Ranu, B. C.; Adak, L.; Banerjee, S. Tetrahedron Lett. 2008, 49, 4613-4617. DOI: 10.1016/j.tetlet.2008.05.083. (d) Ranu, B. C.; Banerjee, S. J. Org. Chem. 2005, 70, 4517-4519. DOI: 10.1021/jo0500885. (e) Ranu, B. C.; Banerjee, S. Org. Lett. 2005, 7, 3049-3052. DOI: 10.1021/ol051004h. (f) Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H. J. Am. Chem. Soc. 2002, 1246, 926-927. DOI: 10.1021/ja017593d. (g) Azizi, N.; Shirdel, F. J. Mol. Liq. 2016, 222, 783-787. DOI: 10.1016/j.molliq.2016.07.128. (h) Zhou, S.; Song, N.; Lv, X.; Jia, Q. Microchim. Acta. 2017, 184, 3497-3504. DOI: 10.1007/s00604-017-2354-5. (i) Azizi, N.; Senejani, M. A.; Abbasi, F. Tetrahedron Lett. 2016, 57, 5009-5011. DOI: 10.1016/j.tetlet.2016.09.099. (j) Sawant, A. D.; Raut, D. G.; Darvatkar, N. B.; Salunkhe, M. M. Green Chem. Lett. Rev. 2011, 4, 41-54. DOI: 10.1080/17518253.2010.500622. (k) Joseph, A.; Żyła, G.; Thomas, V. I.; Nair, P. R.; Padmanabhan, A. S.; Mathew, S. J. Mol. Liq. 2016, 218, 319-331. DOI: 10.1016/j.molliq.2016.02.086. (l) Abbasi, F.; Azizi, N.; Senejani, M. A. Appl. Organometal. Chem. 2017, 31, e3790. DOI: 10.1002/aoc.3790.
  • (a) Conversion of Methyl Ketones into Terminal Acetylenes: Ethynylferrocene. Organic Syntheses Coll. 1998, 9, 411. (b) Conversion of Methyl Ketones into Terminal Acetylenes: Ethynylferrocene. Organic Syntheses Coll. 1996, 73, 262. DOI: 10.15227/orgsyn.073.0262.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.