European Journal of Chemistry 2015, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306

An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity


Abdel-Zaher Abdel-Aziz Elassar (1,*)

(1) Chemistry Department, Faculty of Science, Ain Helwan, Helwan University, Cairo, 11795, Egypt
(*) Corresponding Author

Received: 20 Jul 2015, Accepted: 22 Aug 2015, Published: 31 Dec 2015

Abstract


Tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines afforded in situ N-acylated amines, which undergoes cycloaddition reaction with other molecule of acid chloride to give dihydropyran carboxamide derivatives as an unexpected product. 2-Amino benzimidazole, 2-aminobenzthiazole, 2-aminothiazole, anthranilic acid, o-pheneylenediamine, and 3-methyl-1H-pyrazol-5(4H)-one are reacted with methacryloyl chloride at 0 °C to give different derivatives of dihydropyran carboxamide. The latter compound was obtained through acylation of the organic amines followed by tandem cycloaddition reaction. In contrast acryloyl chloride afforded only N-acylated derivatives. Both products are characterized by single crystal X-ray diffraction method. Bioactivity of the newly synthesized products was studied against Gram-positive, Gram-negative bacteria and fungus.


Keywords


Synthesis; Biological activity; Cycloaddition reaction; Single crystal structure; Tandem cycloaddition reaction; Dihydropyrancarboxamide derivatives

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DOI: 10.5155/eurjchem.6.4.387-393.1306

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References

[1]. Winkler, J. D. Chem. Rev. 1996, 96, 167-176.
http://dx.doi.org/10.1021/cr950029z

[2]. Jana, N.; Zhou, F.; Driver, T. G. J. Am. Chem. Soc. 2015, 137(21), 6738-6741.
http://dx.doi.org/10.1021/jacs.5b02946

[3]. Lee, S. S.; Kim, W. Y.; Lee, H. Y. Chem. An Asian J. 2012, 7(10), 2450-2456.
http://dx.doi.org/10.1002/asia.201200497

[4]. Xie, Y. M.; Yao, Y. Q.; Sun, H. B.; Yan, T. T.; Liu, J.; Kang, T. R. Molecules 2011, 16(10), 8745-8757.
http://dx.doi.org/10.3390/molecules16108745

[5]. Odedra, A.; Wu, C. J.; Pratap, T. B.; Huang, C. W.; Ran, Y. F.; Liu, R. S. J. Am. Chem. Soc. 2005, 127(10), 3406-1412.
http://dx.doi.org/10.1021/ja043047j

[6]. Ho, T. Tandem Organic Reaction; Wiley-Interscience, New York, 1992.

[7]. Bentabed-Ababsa, G.; Derdour, A.; Roisnel, T.; Saez, J. A.; Domingo, L. R.; Mongin, F.; Org. Biomol. Chem. 2008, 6, 3144-3157.
http://dx.doi.org/10.1039/b804856h

[8]. Diels, O.; Alder, K. Liebigs Ann. Chem. 1928, 460, 98-122.
http://dx.doi.org/10.1002/jlac.19284600106

[9]. Danishefsky, S. J.; Larson, E.; Ashkin, D.; Kato, N. J. Am. Chem. Soc. 1985, 107, 1246-1255.
http://dx.doi.org/10.1021/ja00291a026

[10]. Gao, Q.; Maruyama, T.; Mouri, M.; Yamamoto, H. J. Org. Chem. 1992, 57, 1951-1952.
http://dx.doi.org/10.1021/jo00033a005

[11]. Gao, Q.; Ishihars, K.; Maruyama, T.; Mouri, M.; Yamamoto, H. Tetrahedron 1994, 50, 979-988.
http://dx.doi.org/10.1016/S0040-4020(01)80812-7

[12]. Fischer, W.; Bellus, D.; Adler, A.; Francotte, E.; Roloff, A. Chimia 1985, 39, 19-20.

[13]. Warneke, J.; Wang, Z.; Zeller, M.; Leibfritz, D.; Plaumann, M.; Azov, V. A. Tetrahedron 2014, 70, 6515-6521.
http://dx.doi.org/10.1016/j.tet.2014.07.019

[14]. Zeller, M.; Warneke, J.; Azov, V. Acta Crystallogr. E 2014, 70, 121-123.
http://dx.doi.org/10.1107/S1600536814017711

[15]. Nagano, S. Jpn. KokaiTokkyo (2002), JP 2002187868 A 20020705.

[16]. PubChem (CID 13396407; 2007) https://pubchem.ncbi.nlm.nih.gov/compound/13396407 and (CID 641639; 2006); https://pubchem.ncbi.nlm.nih.gov/compound/641639.

[17]. Alder, K.; Reuden, E. Chem. Ber. 1941, 74B, 920-926.
http://dx.doi.org/10.1002/cber.19410740610

[18]. Schulz, H.; Wagner, H. Angew. Chem. 1950, 62, 105-118.
http://dx.doi.org/10.1002/ange.19500620502

[19]. Alder, K.; Offermanns, H.; Ruuden, E. Chem. Ber. 1941, 74B, 905921.

[20]. Whetstone, R. R. Dihydropyran Derivatives, U. S. Patent 2, 479, 283, Aug 16, 1949.

[21]. Stoner, G. G.; McNulty, J. S. J. Am. Chem. Soc. 1950, 72, 1531-1533;
http://dx.doi.org/10.1021/ja01160a028

[22]. Hall, R. H. J. Chem. Soc. 1953, 1398-1402.
http://dx.doi.org/10.1039/jr9530001398

[23]. Crawford, J. W. C. J. Soc. Chem. Ind. 1947, 66, 155-161.
http://dx.doi.org/10.1002/jctb.5000660505

[24]. Albisetti, C. J.; England, D. C.; Hogsed, M. J.; Joyce, R. M. J. Am. Chem. Soc. 1956, 78, 472-475.
http://dx.doi.org/10.1021/ja01583a060

[25]. Alsughayer, A.; Elassar, A. Z. A.; Al Sagheer, F.; Mustafa, S. Pharm. Chem. J. 2012, 46 (7), 418-428.
http://dx.doi.org/10.1007/s11094-012-0813-1

[26]. Elassar, A. Z. A.; El-Sayed, A. E. M.; Ahmed, F. S. J. Appl. Poly. Sci. 2010, 117(1), 200-2010.

[27]. Elassar, A. Z. A.; Al-Fulaij, O. A.; El-Sayed, A. E. M. J. Polym. Res. 2010, 17, 447-458.
http://dx.doi.org/10.1007/s10965-009-9331-6

[28]. Elassar, A. Z. A.; Al Sughayer, A.; Al Sagheer, F. J. Appl. Poly. Sci. 2010, 117 (6), 3679-3686.

[29]. Nakashima, T.; Kamiya, Y.; Iwatsuki, M.; Sato, N.; Takahashi, Y.; Omura, S. J. Antibiotics 2015, 68(3), 220-222.
http://dx.doi.org/10.1038/ja.2014.134

[30]. Ghosh, A. K.; Veitschegger, A. M.; Sheri, V. R.; Effenberger, K. A.; Prichard, B. E.; Jurica, M. S. Org. Lett. 2014, 16(23), 6200-6203.
http://dx.doi.org/10.1021/ol503127r

[31]. Thomas, A. A.; Hunt, K. W.; Volgraf, M.; Watts, R. J.; Liu, X.; Vigers, G.; Smith, D.; Sammond, D.; Tang, T. P.; Rhodes, S. P.; et al J. Med. Chem. 2014, 57(3), 878-902.
http://dx.doi.org/10.1021/jm401635n

[32]. Lagisetti, C.; Yermolina, M. V.; Sharma, L. K.; Palacios, G.; Prigaro, B. J.; Webb, T. R. ACS Chem. Biol. 2014, 9(3), 643-648.
http://dx.doi.org/10.1021/cb400695j

[33]. Gundogdu-Karaburun, N. Lett. Drug Design Disc. 2014, 11(6), 814-823.
http://dx.doi.org/10.2174/1570180811999140515100911

[34]. Liu, Y.; Zhang, L.; Gong, J.; Fang, H.; Liu, A.; Du, G.; Xu, W. J. Enzy. Inhib. Med. Chem. 2011, 26(4), 506-513.
http://dx.doi.org/10.3109/14756366.2010.534732

[35]. Khan, M. A. J. A.; Shafi, S. S. Asian J. Chem. 2003, 15(3-4), 1443-1448.

[36]. Sanfilippo, P. J.; Jetter, M. C.; Cordova, R.; Noe, R. A.; Chourmouzis, E.; Lau, C. Y.; Wang, E. J. Med. Chem. 1995, 38(7), 1057-1059.
http://dx.doi.org/10.1021/jm00007a002

[37]. Hisamoddin, S. Z. K.; Priyanka, S.; Yogesh, S. P.; Nilam, U. P. Pharma Sc. Mon. 2014, 5(1), 207-225.

[38]. Reddy, D. R. S.; Jamullamudi, R. N.; Pedamallu, N.; Rani, A. P. World J. Pharm. Pharm. Sci. 2014, 3(5), 849-856,

[39]. Zhong, K.; Gao, X. L.; Xu, Z. J.; Gao, H.; Fan, S.; Yamaguchi, I.; Li, L. H.; Chen, R. J. Current Res. Bacteriol. 2011, 4(2), 63-72.
http://dx.doi.org/10.3923/crb.2011.63.72

[40]. Pandeya, S. N.; Rai, P. J. Sci. Res. Pharm. 2012, 1(4), 1-4.

[41]. Zhao, Z.; Arnaiz, D. O.; Griedel, B.; Sakata, S.; Dallas, J. L.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M. M. Bioorg. Med. Chem. Lett. 2000, 10(9), 963-966.
http://dx.doi.org/10.1016/S0960-894X(00)00139-6

[42]. Bnina, E. B.; Romdhane, A.; Daami‐Remadi, M.; Jannet, H. B. Eur. J. Chem. 2015, 6(1), 21‐30.
http://dx.doi.org/10.5155/eurjchem.6.1.21-30.1137

[43]. Al-Omran, F.; Elassar, A. Z. A.; El-Khair, A. A. J. Heterocyclic Chem. 2003, 40, 249-254.
http://dx.doi.org/10.1002/jhet.5570400208


How to cite


Elassar, A. Eur. J. Chem. 2015, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306
Elassar, A. An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity. Eur. J. Chem. 2015, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306
Elassar, A. (2015). An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity. European Journal of Chemistry, 6(4), 387-393. doi:10.5155/eurjchem.6.4.387-393.1306
Elassar, Abdel-Zaher. "An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity." European Journal of Chemistry [Online], 6.4 (2015): 387-393. Web. 22 Sep. 2019
Elassar, Abdel-Zaher. "An unexpected tandem cycloaddition reaction of α,β-unsaturated acid chloride with amines: Synthesis of dihydropyrancarboxamide derivatives and biological activity" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

DOI Link: https://doi.org/10.5155/eurjchem.6.4.387-393.1306

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