Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Visible Light Assisted Hantzsch Reaction: Synthesis of Polycyclic Dihydropyridines

Author(s): Ankusab Noorahmadsab Nadaf and Kalegowda Shivashankar*

Volume 16, Issue 8, 2019

Page: [676 - 682] Pages: 7

DOI: 10.2174/1570178615666181107095151

Price: $65

Abstract

The polycyclic dihydropyridine nucleus represents the heterocyclic system of invaluable core motifs with wide applications in chemical, biological and physical properties. Although this kind of compounds have been extensively synthesized by other groups, the synthesis of these compounds under CFL light intensity were not explored. The synthesis of polycyclic dihydropyridine derivatives were achieved through the reaction of 4-hydroxycoumarin, aromatic aldehydes and ammonium acetate under CFL light irradiation conditions. A series of polycyclic dihydropyridine derivatives were prepared under CFL light irradiation conditions with high yield, short reaction time, ambient condition and without the use of catalyst. The results displayed an efficient method for the synthesis of polycyclic dihydropyridine derivatives. Clean profile, short reaction time, low cost and use of CFL light intensity instead of catalyst making it a genuinely green protocol.

Keywords: CFL light, visible light, dihydropyridine, pyridine, coumarin, CFL.

« Previous Next »
Graphical Abstract

[1]
Silva, E.M.P.; Varandas, P.A.M.M.; Silva, A.M.S. Synthesis, 2013, 45, 3053-3089.
[2]
Tejedor, D.; Cotos, L.; Abt, G.M.; Tellado, F.G. J. Org. Chem., 2014, 79, 10655-10661.
[3]
Kidwai, M.; Kukreja, S.; Rastogi, S.; Singhal, K.; Kumar, N. Indian J. Chem., 2014, 53B, 605-609.
[4]
Miri, R.; Javidnia, K.; Sarkarzadch, H.; Hemmateenejad, B. Bioorg. Med. Chem., 2006, 14, 4842-4849.
[5]
Marco-Contelles, J.; León, R. los Ríos, C.D.; Samadi, A.; Bartolini, M.; Andrisano, V.; Huertas, O.; Barri, X.; Luque, F.J.; Rodríguez-Franco, M.I.; López, B.; López, M.G.; García, A.G.; Carreiras, M. D.C.; Villarroya, M. J. Med. Chem., 2009, 52, 2724-2732.
[6]
Drizin, I.; Altenbach, R.J.; Buckner, S.A.; Whiteaker, K.L.; Scott, J.F.; Darbyshire, V.; Jayanti, R.F.; Henry, M.J.; Coghlan, M.; Gopalakrishnan, W.A. Bioorg. Med. Chem., 2004, 12, 1895-1904.
[7]
Carroll, W.A.; Agrios, K.A.; Altenbach, R.J.; Buckner, S.A.; Chen, Y.; Coghlan, M.J.; Daza, A.V.; Drizin, I.; Gopalakrishnan, M.; Henry, R.F.; Kort, M.E.; Kym, P.R.; Milicic, I.; Smith, J.C.; Tang, R.; Turner, S.C.; Whiteaker, K.L.; Zhang, H.; Sullivan, J.P. J. Med. Chem., 2004, 47, 3180-3192.
[8]
Altenbach, R.J.; Brune, M.E.; Buckner, S.A.; Coghlan, M.J.; Daza, A.V.; Fabiyi, A.; Gopalakrishnan, M.; Henry, R.F.; Khilevich, A.; Kort, M.E.; Milicic, I.; Scott, V.E.; Smith, J.C.; Whiteaker, K.L. Carroll. W.A. J. Med. Chem., 2006, 16, 6869-6887.
[9]
Li, M.; Zuo, Z. L.; Wen, S. Wang, S. J. Comb. Chem., 2008, 10, 436-441.
[10]
Nikpassand, M.; Tabatabaeian, K. Molecules, 2009, 14, 1468-1474.
[11]
Kudale, A.A.; Miller, D.O.; Dawea, L.N.; Bodwell, G.J. Org. Biomol. Chem., 2011, 9, 7196-7206.
[12]
Dam, B.; Nandi, S.; Pal, A.K. Tetrahedron Lett., 2014, 55, 5236-5240.
[13]
Kidwai, M.; Rastogi, S.; Mohan, R. Bull. Korean Chem. Soc., 2004, 25, 119-121.
[14]
Nandi, S.; Gupta, A.; Pai, K. Lett. Org. Chem., 2017, 14, 291-299.
[15]
Yang, J.; Jiang, C.; Yang, J.; Qian, C.; Fang, D. Green Chem. Lett. Rev., 2013, 6, 262-267.
[16]
Lavilla, R. J. Chem. Soc., Perkin Trans., 2002, 1, 1141-1156.
[17]
Cui, S.L.; Wang, J.; Lin, X.F.; Wang, Y.G. J. Org. Chem., 2007, 72, 7779-7782.
[18]
Stout, D.M.; Meyers, A.I. Chem. Rev., 1982, 82, 223-243.
[19]
Lee, J.H. Tetrahedron Lett., 2005, 46, 7329-7330.
[20]
Singh, O.M.; Devi, N.S. J. Org. Chem., 2009, 74, 3141-3144.
[21]
Liang, J.C.; Yeh, J.L.; Wang, C.S.; Liou, S.F.; Tsai, C.H.; Chen, I.J. Bioorg. Med. Chem., 2002, 10, 719-730.
[22]
Rafiee, E.; Eavani, S.; Rashidzadeh, S.; Joshaghani, M. Inorg. Chim. Acta, 2009, 362, 3555-3562.
[23]
Baghbanian, S.M.; Khaksar, S.; Vahdat, S.M.; Farhang, M. Tajbakhsh. M. Chin. Chem. Lett., 2010, 21, 563-567.
[24]
Avalani, J.R.; Patel, D.S.; Raval, D.K. J. Chem. Sci., 2012, 124, 1091-1096.
[25]
Reddy, B.P.; Rajesh, K.; Vijayakumar, V. Arabian. J. Chem., 2015, 8, 138-141.
[26]
Sagadevan, A.; Lyu, P.C.; Hwang, K.C. Green Chem., 2016, 18, 4526-4530.
[27]
Xuan, J.; Xia, X.D.; Zeng, T.T.; Feng, Z.J.; Chen, J.R.O.; Lu, L.Q.; Xiao, W.J. Angew. Chem. Int. Ed., 2014, 53, 5653-5656.
[28]
Yin, X.; Li, W.; Jiang, Y.; Zhang, X.; Zhang, L.; Wan, J.; Hu, J.S. ACS Appl. Mater. Interf, 2016, 8, 15258-15266.
[29]
Masuda, Y.; Ishida, N.; Murakami, M. J. Am. Chem. Soc., 2015, 137, 14063-14066.
[30]
Liu, X.; Cong, T.; Liu, P.; Sun, P. J. Org. Chem., 2016, 81, 7256-7261.
[31]
Yasu, Y.; Koike, T.; Akita, M. Chem. Commun., 2013, 49, 2037-2039.
[32]
Liua, W.; Wang, C.; Huang, Y.; Chen, Q.; Wang, L.; He, M. Synth. Commun., 2016, 46, 1268-1274.
[33]
Yang, D.; Huang, B.; Wei, W.; Li, J.; Lin, G.; Liu, Y.; Ding, J.; Sun, P.; Wang, H. Green Chem., 2016, 18, 5630-5634.
[34]
Chen, Y.; Wang, D.H.; Chen, B.; Zhong, J.J.; Tung, C.H.; Wu, L.Z. J. Org. Chem., 2012, 77, 6773-6777.
[35]
Cheng, Y.; Yang, J.; Qu, Y.; Li, P. Org. Lett., 2012, 14, 98-101.
[36]
Helmy, S.; Leibfarth, F.A.; Oh, S.; Poelma, J.E.; Hawker, C.J.; Alaniz, J.R.D. J. Am. Chem. Soc., 2014, 136, 8169-8172.
[37]
Laurier, E.K.G.M.; Vermoortele, F.; Ameloot, R.; Vos, D.E.D.; Hofkens, J.; Roeffaers, M.B.J. J. Am. Chem. Soc., 2013, 135, 14488-14491.
[38]
Liu, G.; Niu, P.; Yin, L.; Cheng, H.M. J. Am. Chem. Soc., 2012, 134, 9070-9073.
[39]
Shamala, D.; Shivashankar, K. Chandra, Mahendra, M. Synth. Commun., 2016, 46, 433-441.
[40]
Shamala, D.; Shivashankar, K. Synth. Commun., 2017, 47, 105-110.
[41]
Shamala, D.; Shivashankar, K. Synth. Commun., 2016, 46, 1735-1740.
[42]
Beerappa, M.; Shivashankar, K. Synth. Commun., 2016, 46, 421-432.
[43]
Beerappa, M.; Shivashankar, K. Synth. Commun., 2018, 48, 146-154.
[44]
Beerappa, M.; Shivashankar, K. J. Heterocyclic. Chem., 2017, 54, 2197-2205.
[45]
Beerappa, M.; Shivashankar, K. Synth. Commun., 2018, 48, 2150-2158.
[46]
Beerappa, M.; Shivashankar, K. RSC Adv, 2015, 5, 30364-30371.
[47]
Jagadishbabu, N.; Shivashankar, K. Lett. Org. Chem., 2017, 14, 330-336.
[48]
Jagadishbabu, N.; Shivashankar, K. J. Chin. Chem. Soc., 2017, 64, 474-480.
[49]
Jagadishbabu, N.; Shivashankar, K. RSC Adv, 2015, 5, 95240-95246.
[50]
Jagadishbabu, N.; Shivashankar, K. Nat. Prod. J., 2018, 8, 201-206.
[51]
Chacko, P.; Shivashankar, K. Tetrahedron, 2018, 74, 1520-1526.
[52]
Chacko, P.; Shivashankar, K. Chin. Chem. Lett., 2017, 28, 1619-1624.
[53]
Chacko, P.; Shivashankar, K. Synth. Commun., 2018, 48, 1363-1376.
[54]
Jayashree, S.; Shivashankar, K. Synth. Commun., 2018, 48, 1805-1815.
[55]
Shivashankar, K.; Kulkarni, M.V.; Shastri, L.A.; Rasal, V.P.; Saindane, D.M. J. Indian Chem. Soc., 2009, 86, 265-271.
[56]
Shivashankar, K.; Kulkarni, M.V.; Shastri, L.A.; Rasal, V.P.; Saindane, D.M. J. Indian Chem. Soc., 2008, 85, 1163-1168.
[57]
Shivashankar, K.; Kulkarni, M.V.; Shastri, L.A.; Rasal, V.P.; Rajendra, S.V. Phosphorus Sulfur Silicon, 2008, 183, 56-68.
[58]
Shivashankar, K.; Kulkarni, M.V.; Shastri, L.A.; Rasal, V.P.; Rajendra, S.V. Phosphorus Sulfur Silicon., 2006, 181, 2187-2200.
[59]
Shastri, L.A.; Shivashankar, K.; Kulkarni, M.V. J. Sulfur Chem., 2007, 28, 625-630.
[60]
Tiwari, J.; Saquib, M.; Singh, S.; Tufail, F.; Singh, M.; Singh, J.; Singh, J. Green Chem., 2016, 18, 3221-3231.
[61]
Hari, D.P.; Konig, B.; Eosin, Y. Org. Lett., 2011, 13, 3852-3855.
[62]
Hoffmann, N. Chem. Rev., 2008, 108, 1052-1103.
[63]
Pike, S.J.; Hutchinson, J.J.; Hunter, C.A. J. Am. Chem. Soc., 2017, 139, 6700-6706.
[64]
Brahmbhatt, D.I.; Pandya, U.R.; Raolji, G.B. Heterocycl. Commun., 2004, 10, 419-422.
[65]
Qadir, S.; Khan, K.Z. Jan. A. Asian J. Chem., 2013, 25, 3019-3022.
[66]
Jagadishbabu, N.; Shivashankar, K. J. Heterocycl. Chem., 2017, 54, 1543-1549.
[67]
Nadaf, A.N.; Shivashankar, K. Synth. Commun., 2018, 48, 809-815.
[68]
Nadaf, A.N.; Shivashankar, K. J. Heterocycl. Chem., 2018, 55, 1375-1381.
[69]
Zhang, M.; Fu, Q.Y.; Gao, G.; He, H.Y.; Zhang, Y.; Wu, Y.S.; Zhang, Z.H. ACS Sustain. Chem. Eng., 2017, 5, 6175-6182.

Rights & Permissions Print Cite
Article Metrics
53
2
© 2024 Bentham Science Publishers | Privacy Policy