Download PDF
Synthesis 2023; 55(17): 2691-2701
DOI: 10.1055/a-2075-3140
paper

A New Domino Reaction under Microwave Irradiation for the Synthesis of Pyrazolo[5,1-b]quinazolinones

Jia Hui Ng
a   School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
,
Felicia Phei Lin Lim
a   School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
,
Edward R. T. Tiekink
b   Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, 5 Jalan Universiti, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
,
Anton V. Dolzhenko  ∗
a   School of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway, Selangor Darul Ehsan 47500, Malaysia
c   Curtin Medical School, Curtin Health Innovation Research Institute, Faculty of Health Sciences, Curtin University, GPO Box U1987 Perth, Western Australia 6845, Australia
› Author AffiliationsThis work is supported by the Ministry of Higher Education, Malaysia under the Fundamental Research Grant Scheme (Grant no. FRGS/1/2020/STG04/MUSM/02/2). Sunway University Sdn Bhd is thanked for financial support of the X-ray crystallographic study (Grant no. GRTIN-RRO-56-2022).
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Pyrazolo[5,1-b]quinazolinones were synthesized by consecutive pyrazole and quinazolinone ring closures in a new catalyst-free microwave-promoted domino reaction of hydrazine with 2-cyano-3-(methylthio)-3-(2-methoxycarbonylphenylamino)acrylates, which were prepared from methyl anthranilate and 2-cyano-3,3-bis(methylthio)acrylates. When 2-cyano-3,3-bis(methylthio)acrylates reacted directly with anthranilic acid hydrazide, the arylamino group remained intact, while the hydrazide moiety transformed into 1-acylpyrazoles and further to 2-(1,3,4-oxadiazolylidene)-2-cyanoacetates. The structures of representatives from each group of the prepared heterocyclic compounds were examined in detail by X-ray crystallography.

Key words

pyrazoles - quinazolines - domino reaction - oxadiazolines - anthranilates - microwave-assisted synthesis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2075-3140.
  • Supporting Information


Publication History

Received: 22 February 2023

Accepted after revision: 17 April 2023

Accepted Manuscript online:
17 April 2023

Article published online:
11 May 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Miller JR, Thanabal V, Melnick MM, Lall M, Donovan C, Sarver RW, Lee D.-Y, Ohren J, Emerson D. Chem. Biol. Drug Des. 2010; 75: 444
    CrossrefPubMed
  • 2 Chaudhury S, Abdulhameed MD. M, Singh N, Tawa GJ, D’haeseleer PM, Zemla AT, Navid A, Zhou CE, Franklin MC, Cheung J, Rudolph MJ, Love J, Graf JF, Rozak DA, Dankmeyer JL, Amemiya K, Daefler S, Wallqvist A. PLoS ONE 2013; 8: e63369
    CrossrefPubMed
  • 3 Kapoor TM. World Patent WO2018213712, 2018 ; Chem. Abstr. 2019, 170, 30092
    PubMed
  • 4 Sircar JC, Capiris T, Kesten SJ, Herzig DJ. J. Med. Chem. 1981; 24: 735
    CrossrefPubMed
  • 5 Shaaban MA, Kamal AM, Faggal SI, Farag NA, Aborehab NM, Elsahar AE, Mohamed KO. Arch. Pharm. 2020; 353: 2000027
    CrossrefPubMed
  • 6 Spiegel K, Agrafiotis D, Caprathe B, Davis RE, Dickerson MR, Fergus JH, Hepburn TW, Marks JS, Vandorf M, Wieland DM, Jaen JC. Biochem. Biophys. Res. Commun. 1995; 217: 488
    CrossrefPubMed
  • 7 Colquhoun A, Lawrance GM, Shamovsky IL, Riopelle RJ, Ross GM. J. Pharmacol. Exp. Ther. 2004; 310: 505
    CrossrefPubMed
  • 8 Hefti FF, Rosenthal A, Walicke PA, Wyatt S, Vergara G, Shelton DL, Davies AM. Trends Pharmacol. Sci. 2006; 27: 85
    CrossrefPubMed
  • 9 Eibl JK, Strasser BC, Ross GM. Eur. J. Pharmacol. 2013; 708: 30
    CrossrefPubMed
  • 10 Sircar JC, Capiris T, Kesten SJ. J. Heterocycl. Chem. 1981; 18: 117
    Crossref
  • 11 Beam CF, Brown J, Dawkins DR, Fives WP, Fleindel ND. J. Heterocycl. Chem. 1979; 16: 957
    Crossref
  • 12 Peet NP, Huber EW. Heterocycles 1993; 35: 315
    Crossref
  • 13 Chen D.-S, Zhang M.-M, Li Y.-L, Liu Y, Wang X.-S. Tetrahedron 2014; 70: 2889
    Crossref
  • 14 Zhang Y, Xu J, Li C, Wang X.-S. Tetrahedron 2015; 71: 8732
    Crossref
  • 15 Zhang Y, Shao Y, Gong J, Zhu J, Cheng T, Chen J. J. Org. Chem. 2019; 84: 2798
    CrossrefPubMed
  • 16 Qiao R, Chen J, Chen F, Yang W, Wu H. China Patent CN104725385, 2015 ; Chem. Abstr. 2015, 163, 174572
    PubMed
  • 17 Zhou Y.-J, Zhang M.-M, Li Y.-L, Liu Y, Wang X.-S. Tetrahedron 2014; 70: 3440
    Crossref
  • 18 Dunker C, Imberg L, Siutkina AI, Erbacher C, Daniliuc CG, Karst U, Kalinin DV. Pharmaceuticals 2022; 15: 1340
    CrossrefPubMed
  • 19 Ng JH, Tiekink ER. T, Dolzhenko AV. RSC Adv. 2022; 12: 8323
    CrossrefPubMed
  • 20 Lim FP. L, Gan RX. Y, Dolzhenko AV. Tetrahedron Lett. 2017; 58: 775
    Crossref
  • 21 Jochheim M, Krug HG, Neidlein R, Krieger C. Heterocycles 1995; 41: 1235
    Crossref
  • 22 Zabiulla, Gulnaz AR, Mohammed YH. E, Khanum SA. Bioorg. Chem. 2019; 92: 103220
    CrossrefPubMed
  • 23 Li J.-F, Zhu Y.-Q, Wang X, Yang H.-Z. J. Heterocycl. Chem. 2007; 44: 749
    Crossref
  • 24 Li M, Wen L.-R, Fu W.-J, Zhao G.-L, Hu F.-Z, Yang H.-Z. Chin. J. Chem. 2004; 22: 1064
    Crossref
  • 25 Peseke K. Z. Chem. 1977; 17: 262
    Crossref
  • 26 CrysAlisPro. Rigaku Oxford Diffraction; Yarnton, Oxfordshire: 2017
    Google Scholar
  • 27 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112
    CrossrefPubMed
  • 28 Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
    CrossrefPubMed
  • 29 Farrugia LJ. J. Appl. Crystallogr. 2012; 45: 849
    CrossrefPubMed
  • 30 Brandenburg K. Diamond Version 3.1c . Crystal Impact GbR; Bonn: 2006
    Google Scholar
  • 31 Spek AL. Acta Crystallogr., Sect. E 2020; 76: 1
    CrossrefPubMed
  • 32 CCDC 2011234 (7a), CCDC 2242095 (8a), and CCDC 2242096 (9b) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.