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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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Isolation of intermediates in the synthesis of new 3,4-dihydro-2H-chromeno[2,3-d]pyrimidines

Mehri Fattahi / Abolghasem Davoodnia
  • Corresponding author
  • Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, I. R. Iran, Tel.: +98 51 38435000, Fax: +98 51 38429520, E-mail:
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/ Mehdi Pordel / S. Ali Beyramabadi / Niloofar Tavakoli-Hoseini
  • Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, Mashhad, I. R. Iran
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Published Online: 2018-07-05 | DOI: https://doi.org/10.1515/znb-2018-0042

Abstract

Reaction of N-alkyl-2-imino-2H-chromene-3-carboxamides with dimethyl acetylenedicarboxylate (DMAD) in the presence of sodium carbonate as catalyst in refluxing ethanol gave new tricyclic products identified as methyl 3-alkyl-2-(2-methoxy-2-oxoethyl)-4-oxo-3,4-dihydro-2H-chromeno[2,3-d]pyrimidine-2-carboxylates. In the absence of sodium carbonate, dimethyl 2-((E)-3-(alkylcarbamoyl)-2H-chromen-2-ylideneamino)fumarates were isolated as intermediates. These intermediates could be successfully converted to the same new tricyclic products by heating in ethanol containing sodium carbonate. All new synthetic compounds were characterized on the basis of their FT-IR, 1H and 13C NMR spectra, and microanalytical data. To identify the correct stereoisomer of the intermediates, in one case a 2D nuclear Overhauser effect (2D-NOESY) spectrum together with density functional theory (DFT) calculation at the B3LYP/6-311+G(d,p) level of theory was used.

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This article offers supplementary material which is provided at the end of the article.

Keywords: 2D-NOESY; chromeno[2,3-d]pyrimidines; DFT; DMAD; sodium carbonate

References

  • [1]

    A. M. Shestopalov, Y. M. Litvinov, L. A. Rodinovskaya, O. R. Malyshev, M. N. Semenova, V. V. Semenov, ACS Comb. Sci. 2012, 14, 484.CrossrefGoogle Scholar

  • [2]

    S. A. Patil, J. Wang, X. S. Li, J. Chen, T. S. Jones, A. Hosni-Ahmed, R. Patil, W. L. Seibel, W. Li, D. D. Miller, Bioorg. Med. Chem. Lett. 2012, 22, 4458.CrossrefGoogle Scholar

  • [3]

    O. S. Patrusheva, V. V. Zarubaev, A. A. Shtro, Y. R. Orshanskaya, S. A. Boldyrev, I. V. Ilyina, S. Y. Kurbakova, D. V. Korchagina, K. P. Volcho, N. F. Salakhutdinov, Bioorg. Med. Chem. 2016, 24, 5158.CrossrefGoogle Scholar

  • [4]

    A. Parthiban, J. Muthukumaran, A. Manhas, K. Srivastava, R. Krishna, H. S. P. Rao, Bioorg. Med. Chem. Lett. 2015, 25, 4657.CrossrefGoogle Scholar

  • [5]

    L. C. Rao, N. S. Kumar, V. Dileepkumar, U. S. N. Murthy, H. M. Meshram, RSC Adv. 2015, 5, 28958.CrossrefGoogle Scholar

  • [6]

    G. Zhang, Y. Zhang, J. Yan, R. Chen, S. Wang, Y. Ma, R. Wang, J. Org. Chem. 2012, 77, 878.CrossrefGoogle Scholar

  • [7]

    M. A. Abdelgawad, H. A. H. Elshemy, K. R. A. Abdellatif, H. A. Omar, J. Chem. Pharm. Res. 2013, 5, 387.Google Scholar

  • [8]

    C. W. Johannes, M. S. Visser, G. S. Weatherhead, A. H. Hoveyda, J. Am. Chem. Soc. 1998, 120, 8340.CrossrefGoogle Scholar

  • [9]

    M. A. Bhat, N. Siddiqui, S. A. Khan, Acta Pol. Pharm. 2008, 65, 235.Google Scholar

  • [10]

    D. Zhang, Y. Ma, Y. Liu, Z.-P. Liu, Arch. Pharm. (Weinheim, Ger.) 2014, 347, 576.CrossrefGoogle Scholar

  • [11]

    D. C. Karia, H. K. Pandya, N. K. Godvani, Asian J. Biochem. Pharm. Res. 2012, 2, 126.Google Scholar

  • [12]

    T. Narender, Shweta, S. Gupta, Bioorg. Med. Chem. Lett. 2004, 14, 3913.CrossrefGoogle Scholar

  • [13]

    O. Perumal, S. V. K. Peddakotla, L. Suresh, G. V. P. Chandramouli, Y. Pydisetty, J. Biomol. Struct. Dyn. 2017, 35, 2620.CrossrefGoogle Scholar

  • [14]

    İ. Esirden, M. Tanç, C. T. Supuran, M. Kaya, Bioorg. Med. Chem. Lett. 2017, 27, 86.CrossrefGoogle Scholar

  • [15]

    G. Gopinath, V. Sankeshi, S. Perugu, M. D. Alaparthi, S. Bandaru, V. K. Pasala, P. R. Chittineni, G. L. D. Krupadanam, S. R. Sagurthi, Eur. J. Med. Chem. 2016, 124, 750.CrossrefGoogle Scholar

  • [16]

    M. Choi, Y.-S. Hwang, A. S. Kumar, H. Jo, Y. Jeong, Y. Oh, J. Lee, J. Yun, Y. Kim, S.-B. Han, J.-K. Jung, J. Cho, H. Lee, Bioorg. Med. Chem. Lett. 2014, 24, 2404.CrossrefGoogle Scholar

  • [17]

    A. Fallah-Tafti, R. Tiwari, A. N. Shirazi, T. Akbarzadeh, D. Mandal, A. Shafiee, K. Parang, A. Foroumadi, Med. Chem. 2011, 7, 466.CrossrefGoogle Scholar

  • [18]

    J. F. Cheng, A. Ishikawa, Y. Ono, T. Arrhenius, A. Nadzan, Bioorg. Med. Chem. Lett. 2003, 13, 3647.CrossrefGoogle Scholar

  • [19]

    L. R. Gomes, J. N. Low, F. Cagide, D. Chavarria, F. Borges, Acta Crystallogr. 2015, E71, 547.Google Scholar

  • [20]

    G. P. Ellis, in The Chemistry of Heterocyclic Compounds (Eds.: A. Weissberger, E. C. Taylor), John Wiley, New York, 1977, chapter II, pp. 11–139.Google Scholar

  • [21]

    D. G. Krotko, K. V. Fedotov, A. D. Kachkovski, A. I. Tolmachev, Dyes Pigm. 2005, 64, 79.CrossrefGoogle Scholar

  • [22]

    E. A. A. Hafez, M. H. Elnagdi, A. G. A. Elagamey, F. M. A. A. El-Taweel, Heterocycles 1987, 26, 903.CrossrefGoogle Scholar

  • [23]

    Y. Guo, S.-Q. Wang, Z.-Q. Ding, J. Zhou, B.-F. Ruan, J. Organomet. Chem. 2017, 851, 150.CrossrefGoogle Scholar

  • [24]

    H. Atapour-Mashhad, Z. Tayarani-Najaran, A. Davoodnia, R. Moloudi, S. H. Mousavi, Drug Chem. Toxicol. 2011, 34, 271.CrossrefGoogle Scholar

  • [25]

    D. Yao, Y. Zhou, L. Zhu, L. Ouyang, J. Zhang, Y. Jiang, Y. Zhao, D. Sun, S. Yang, Y. Yu, J. Wang, Eur. J. Med. Chem. 2017, 140, 155.CrossrefGoogle Scholar

  • [26]

    M. M. M. Ramiz, W. A. El-Sayed, E. Hagag, A. A. H. Abdel-Rahman, J. Heterocycl. Chem. 2011, 48, 1028.CrossrefGoogle Scholar

  • [27]

    S. Vazirimehr, A. Davoodnia, S. A. Beyramabadi, M. Nakhaei-Moghaddam, N. Tavakoli-Hoseini, Z. Naturforsch. 2017, 72b, 481.Google Scholar

  • [28]

    A. Agarwal, Ramesh, Ashutosh, N. Goyal, P. M. S. Chauhan, S. Gupta, Bioorg. Med. Chem. 2005, 13, 6678.CrossrefGoogle Scholar

  • [29]

    E. P. D. S. Falcao, S. J. De Melo, R. M. Srivastava, M. T. Catanho, S. C. Nascimento, Eur. J. Med. Chem. 2006, 41, 276.CrossrefGoogle Scholar

  • [30]

    Q. Chen, X. Zhu, L. Jiang, L. M. Yang, G. Fu, Eur. J. Med. Chem. 2008, 43, 595.CrossrefGoogle Scholar

  • [31]

    N. C. Desai, G. M. Kotadiya, A. R. Trivedi, Bioorg. Med. Chem. Lett. 2014, 24, 3126.CrossrefGoogle Scholar

  • [32]

    K. Yalagala, S. B. Jonnalagadda, S. Maddila, S. Rana, S. N. Maddila, Lett. Drug Des. Discovery 2017, 14, 763.Google Scholar

  • [33]

    A. H. Halawa, M. M. Elaasser, A. M. El Kerdawy, A. M. A. I. Abd El-Hady, H. A. Emam, A. M. El-Agrody, Med. Chem. Res. 2017, 26, 2624.CrossrefGoogle Scholar

  • [34]

    N. R. Kamdar, D. D. Haveliwala, P. T. Mistry, S. K. Patel, Med. Chem. Res. 2011, 20, 854.CrossrefGoogle Scholar

  • [35]

    A. J. Patel, M. P. Patel, Indian Drugs 2017, 54, 16.Google Scholar

  • [36]

    A. M. El-Agrody, A. H. Halawa, A. M. Fouda, A.-A. M. Al-Dies, J. Saudi Chem. Soc. 2017, 21, 82.CrossrefGoogle Scholar

  • [37]

    S. Ameli, M. Pordel, A. Davoodnia, M. Jajarmi, Russ. J. Bioorg. Chem. 2017, 43, 429.CrossrefGoogle Scholar

  • [38]

    A. Davoodnia, M. Rahimizadeh, Sh. Rivadeh, M. Bakavoli, M. Roshani, Indian J. Heterocycl. Chem. 2006, 16, 151.Google Scholar

  • [39]

    N. Seifi, M. H. Zahedi-Niaki, M. Reza Barzegari, A. Davoodnia, R. Zhiani, A. A. Kaju, J. Mol. Catal. A: Chem. 2006, 260, 77.CrossrefGoogle Scholar

  • [40]

    A. Davoodnia, H. Behmadi, A. Zare Bidaki, M. Bakavoli, N. Tavakoli Hoseini, Chin. Chem. Lett. 2007, 18, 1163.CrossrefGoogle Scholar

  • [41]

    A. Davoodnia, M. Roshani, E. Saleh Nadim, M. Bakavoli, N. Tavakoli Hoseini, Chin. Chem. Lett. 2007, 18, 1327.CrossrefGoogle Scholar

  • [42]

    A. Davoodnia, M. Bakavoli, S. Mohseni, N. Tavakoli-Hoseini, Monatsh. Chem. 2008, 139, 963.CrossrefGoogle Scholar

  • [43]

    N. Tavakoli-Hoseini, M. M. Heravi, F. F. Bamoharram, A. Davoodnia, M. Ghassemzadeh, J. Mol. Liq. 2011, 163, 122.CrossrefGoogle Scholar

  • [44]

    M. Khashi, A. Davoodnia, V. S. Prasada Rao Lingam, Res. Chem. Intermed. 2015, 41, 5731.CrossrefGoogle Scholar

  • [45]

    A. Davoodnia, A. Nakhaei, N. Tavakoli-Hoseini, Z. Naturforsch. 2016, 71b, 219.Google Scholar

  • [46]

    S. Vazirimehr, A. Davoodnia, M. Nakhaei-Moghaddam, N. Tavakoli-Hoseini, Heterocycl. Commun. 2017, 23, 65.Google Scholar

  • [47]

    N. Karimi, A. Davoodnia, M. Pordel, Heterocycl. Commun. 2018, 24, 31.CrossrefGoogle Scholar

  • [48]

    D. Guo, T. Chen, D. Ye, J. Xu, H. Jiang, K. Chen, H. Wang, H. Liu, Org. Lett. 2011, 13, 2884.CrossrefGoogle Scholar

  • [49]

    M. Fattahi, A. Davoodnia, M. Pordel, N. Tavakoli-Hoseini, Heterocycl. Lett. 2017, 7, 613.Google Scholar

  • [50]

    M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03 (revision B. 05), Gaussian, Inc., Pittsburgh, PA (USA) 2003.Google Scholar

  • [51]

    C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.CrossrefGoogle Scholar

About the article

Received: 2018-02-17

Accepted: 2018-04-22

Published Online: 2018-07-05


Citation Information: Zeitschrift für Naturforschung B, 20180042, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0042.

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