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Letters in Organic Chemistry

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

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Letter Article

DMAP-Promoted Cascade Reaction of α-Ketoester with Benzylidene- Malononitrile: Access Polyfunctionalized 2-Amino-3-Cyano-4H-Pyran Containing Ester Motifs

Author(s): Chuan-Bao Zhang*, Hong-Tao Wang, Ze-Yue Zhao, Li-Fang Lou, Jiang-Tao Zhao, Yang Geng, Bai-Qiang Zhai and Ye Tian*

Volume 20, Issue 6, 2023

Published on: 27 February, 2023

Page: [495 - 500] Pages: 6

DOI: 10.2174/1570178620666230131145824

Price: $65

Abstract

A base-promoted cascade reaction of α-ketoester with benzylidene-malononitrile was developed under mild reaction conditions, which enabled the synthesis of polyfunctionalized 2-amino- 3-cyano-4H-pyrans containing ester motifs at 6-position with good to excellent yields. These transformations not only construct various polyfunctionalized 4H-pyrans, which add a new member to the family of 4H-pyrans, but also provide an efficient approach for the synthesis of fully substituted 4Hpyran derivatives.

Keywords: Cascade reaction, polyfunctionalized 4H-pyrans, α-Ketoester, benzylidene-malononitrile, 2-Amino-3-cyano-4Hpyrans, multi-component one-pot cascade reaction.

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[1]
Thakur, A.; Pereira, G.; Patel, C.; Chauhan, V.; Dhaked, R.K.; Sharma, A. J. Mol. Struct., 2020, 1206, 127686-127698.
[http://dx.doi.org/10.1016/j.molstruc.2020.127686]
[2]
Doshi, J.M.; Tian, D.; Xing, C. J. Med. Chem., 2006, 49(26), 7731-7739.
[http://dx.doi.org/10.1021/jm060968r] [PMID: 17181155]
[3]
Aridoss, G.; Zhou, B.; Hermanson, D.L.; Bleeker, N.P.; Xing, C. J. Med. Chem., 2012, 55(11), 5566-5581.
[http://dx.doi.org/10.1021/jm300515q] [PMID: 22582991]
[4]
Pavlovska, T.L.; Redkin, R.G.; Lipson, V.V.; Atamanuk, D.V. Mol. Divers., 2016, 20(1), 299-344.
[http://dx.doi.org/10.1007/s11030-015-9629-8] [PMID: 26419598]
[5]
Xie, Y.S.; Ma, C.C.; Wei, Q.Q.; Wang, Y.B.; Zhu, J.Y.; Fu, J.Y.; Yuan, J.F. ChemistrySelect, 2019, 4(21), 6484-6487.
[http://dx.doi.org/10.1002/slct.201901036]
[6]
Cai, Y-H.; Xie, Y-S.; Li, R.; Fan, M-M.; Li, J-J.; Zhang, C-B. Heterocycles, 2021, 102(6), 1175-1184.
[7]
Pratap, U.R.; Jawale, D.V.; Netankar, P.D.; Mane, R.A. Tetrahedron Lett., 2011, 52(44), 5817-5819.
[http://dx.doi.org/10.1016/j.tetlet.2011.08.135]
[8]
Kalla, R.M.N.; Kim, M.R.; Kim, I. Tetrahedron Lett., 2015, 56(5), 717-720.
[http://dx.doi.org/10.1016/j.tetlet.2014.12.079]
[9]
Nagaraju, S.; Paplal, B.; Sathish, K.; Giri, S.; Kashinath, D. Tetrahedron Lett., 2017, 58(44), 4200-4204.
[http://dx.doi.org/10.1016/j.tetlet.2017.09.060]
[10]
Niknam, K.; Jamali, A. Chin. J. Catal., 2012, 33(11-12), 1840-1849.
[http://dx.doi.org/10.1016/S1872-2067(11)60457-9]
[11]
Gein, V.L.; Zamaraeva, T.M.; Slepukhin, P.A. Tetrahedron Lett., 2014, 55(33), 4525-4528.
[http://dx.doi.org/10.1016/j.tetlet.2014.06.077]
[12]
Daloee, T.S.; Behbahani, F.K. Polycycl. Aromat. Compd., 2022, 42(3), 681-689.
[http://dx.doi.org/10.1080/10406638.2020.1749090]
[13]
Dekamin, M.G.; Eslami, M. Green Chem., 2014, 16(12), 4914-4921.
[http://dx.doi.org/10.1039/C4GC00411F]
[14]
Davarpanah, J.; Kiasat, A.R. RSC Advances, 2014, 4(9), 4403-4412.
[http://dx.doi.org/10.1039/C3RA43443E]
[15]
Dabiri, M.; Bahramnejad, M.; Baghbanzadeh, M. Tetrahedron, 2009, 65(45), 9443-9447.
[http://dx.doi.org/10.1016/j.tet.2009.08.070]
[16]
Zhu, S.L.; Ji, S.J.; Zhang, Y. Tetrahedron, 2007, 63(38), 9365-9372.
[http://dx.doi.org/10.1016/j.tet.2007.06.113]
[17]
Khan, T.; Siddiqui, Z.N. New J. Chem., 2014, 38(10), 4847-4858.
[http://dx.doi.org/10.1039/C4NJ00529E]
[18]
Babaei, P. Safaei-Ghomi. J. Mater. Chem. Phys., 2021, 267, 124668-124679.
[http://dx.doi.org/10.1016/j.matchemphys.2021.124668]
[19]
Peiman, S.; Baharfar, R.; Maleki, B. Mater. Today Commun., 2021, 26, 101759-101771.
[http://dx.doi.org/10.1016/j.mtcomm.2020.101759]
[20]
Hallaoui, A.E.; Chehab, S.; Ghailane, T.; Malek, B.; Zimou, O.; Boukhriss, S.; Souizi, A.; Ghailane, R. Polycycl. Aromat. Compd., 2021, 41(10), 2083-2102.
[http://dx.doi.org/10.1080/10406638.2019.1710853]
[21]
Yazdanseta, S.; Yasin, K.; Setoodehkhah, M.; Ghanbari, M.; Fadaee, E. Res. Chem. Intermed., 2022, 48(7), 3039-3060.
[http://dx.doi.org/10.1007/s11164-022-04732-7]
[22]
Paul, S.; Ghosh, S.; Bhattacharyya, P.; Das, A.R. RSC Advances, 2013, 3(34), 14254-14262.
[http://dx.doi.org/10.1039/c3ra42352b]
[23]
Qareaghaj, O.H.; Mashkouri, S.; Naimi-Jamal, M.R.; Kaupp, G. RSC Advances, 2014, 4(89), 48191-48201.
[http://dx.doi.org/10.1039/C4RA06603K]
[24]
Gutierrez, L.F.; Nope, E.; Rojas, H.A.; Cubillos, J.A.; Sathicq, Á.G.; Romanelli, G.P.; Martínez, J.J. Res. Chem. Intermed., 2018, 44(9), 5559-5568.
[http://dx.doi.org/10.1007/s11164-018-3440-y]
[25]
Rostami, N.; Dekamin, M.G.; Valiey, E.; Fanimoghadam, H. Sci. Rep., 2022, 12(1), 8642.
[http://dx.doi.org/10.1038/s41598-022-10774-z] [PMID: 35606381]
[26]
Ghassemi, M.; Maleki, A. SynOpen, 2021, 5(2), 100-103.
[http://dx.doi.org/10.1055/a-1469-6721]
[27]
Chen, M.N.; Di, J.Q.; Li, J.M.; Mo, L.P.; Zhang, Z.H. Tetrahedron, 2020, 76(14), 131059-131069.
[http://dx.doi.org/10.1016/j.tet.2020.131059]
[28]
Sheverdov, V.P.; Andreev, A.Y.; Nasakin, O.E.; Gein, V.L. Pharm. Chem. J., 2014, 48(6), 379-382.
[http://dx.doi.org/10.1007/s11094-014-1114-7]
[29]
Mar’yasov, M.A.; Davydova, V.V.; Sheverdov, V.P.; Nasakin, O.E.; Gein, V.L. Pharm. Chem. J., 2016, 50(8), 519-522.
[http://dx.doi.org/10.1007/s11094-016-1480-4]
[30]
Auria-Luna, F. Sci. Rep., 2020, 11594-11610.
[http://dx.doi.org/10.1038/s41598-020-68076-1] [PMID: 32665694]
[31]
Chang, L.C.W.; von Frijtag Drabbe Künzel, J.K.; Mulder-Krieger, T.; Spanjersberg, R.F.; Roerink, S.F.; van den Hout, G.; Beukers, M.W.; Brussee, J.; IJzerman, A.P. J. Med. Chem., 2005, 48(6), 2045-2053.
[http://dx.doi.org/10.1021/jm049597+] [PMID: 15771447]

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