Download PDF
Synlett 2023; 34(17): 2052-2058
DOI: 10.1055/a-2107-5653
letter

DMAP-Catalyzed Domino Reactions of α-Chloroaldoxime O-Methanesulfonates and 2-Aminobenzoic Acids for the Synthesis of Quinazolinediones

Watcharadet Kaewman
,
Juthanat Kaeobamrung∗
This work was supported by Thailand Research Fund (Grant Number MRG6180298). Further support was generously provided by the Development and Promotion of Science and Technology Talent Project (DPST) for Mr. Kaewman. J.K. also thank the Faculty of Science, ­Research Fund.
› Further Information
    Permissions and Reprints All articles of this category


Abstract

Quinazolinedione derivatives were obtained from 2-aminobenzoic acids and bench-stable α-chloroaldoxime O-methanesulfonates via DMAP-catalyzed domino reactions under mild reaction conditions in one-pot fashion. Chemical transformations involved nucleophilic substitution, Tiemann rearrangement, and cyclic urea formation. The strength of nitrogen nucleophile of 2-aminobenzoic acids and the high level of carbon electrophile of α-chloroaldoxime O-methanesulfonates were crucial for the reaction outcome. An application to synthesize a quinazolinedione building block was introduced.

Key words

quinazolinediones - cylic ureas - organocatalysis - intramolecular C–N amide bond formation - Tiemann rearrangement

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2107-5653.
  • Supporting Information


Publication History

Received: 20 May 2023

Accepted after revision: 07 June 2023

Accepted Manuscript online:
07 June 2023

Article published online:
26 July 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

  • 2 Abdelmonsef AH, Mosallam AM. J. Heterocycl. Chem. 2020; 57: 1
    CrossrefPubMedSearch in Google Scholar
  • 3 Ismail MA. H, Barker S, Abou El Ella DA, Abouzid KA. M, Toubar RA, Todd MH. J. Med. Chem. 2006; 49: 1526
    CrossrefPubMedSearch in Google Scholar
    • 4a Ellsworth EL, Tran TP, Hollis Showalter HD, Sanchez JP, Watson BM, Stier MA, Singh R. J. Med. Chem. 2006; 49: 6435
      CrossrefPubMedSearch in Google Scholar
    • 4b Jiang Z.-Y, Hong WD, Cui X.-P, Gao H.-C, Wu P.-P, Chen Y.-S, Shen D, Yang Y, Zhang B.-J, Taylor MJ, Ward SA, O’Neill PM, Zhao S.-Q, Zhang K. RSC Adv. 2017; 7: 52227
      CrossrefSearch in Google Scholar
  • 5 Bouchut A, Rotili D, Pierrot C, Valente S, Lafitte S, Schultz J, Hoglund U, Mazzone R, Lucidi A, Fabrizi G, Pechalrieu D, Arimondo PB, Skinner-Adams TS, Chua MJ, Andrews KT, Mai A, Khalife J. Eur. J. Med. Chem. 2019; 161: 277
    CrossrefPubMedSearch in Google Scholar
  • 6 Crespo I, Giménez-Dejoz J, Porté S, Cousido-Siah A, Mitschler A, Podjarny A, Pratsinis H, Kletsas D, Parés X, Ruiz FX, Metwally K, Farrés J. Eur. J. Med. Chem. 2018; 152: 160
    CrossrefPubMedSearch in Google Scholar
  • 9 Chen H, Li P, Qin R, Yan H, Li G, Huang H. ACS Omega 2020; 5: 9614
    CrossrefPubMedSearch in Google Scholar
  • 11 Kaeobamrung J, Lanui A, Mahawong S, Duangmak W, Rukachaisirikul V. RSC Adv. 2015; 5: 58587
    CrossrefPubMedSearch in Google Scholar
  • 13 Byrne FP, Jin S, Paggiola G, Petchey TH. M, Clark JH, Farmer TJ, Thomas J, Hunt AJ, Robert MC, Sherwood J. Sustainable Chem. Processes 2016; 4: 7
    CrossrefSearch in Google Scholar
  • 14 Duangjan C, Rukachaisirikul V, Kaeobamrung J. Tetrahedron Lett. 2020; 61: 152330
    CrossrefSearch in Google Scholar
  • 15 Alternative amidoxime rearrangement: Lin C.-C, Hsieh T.-H, Liao P.-Y, Liao Z.-Y, Chang C.-W, Shih Y.-C, Yeh W.-H, Chien T.-C. Org. Lett. 2014; 16: 892
    CrossrefPubMedSearch in Google Scholar
  • 16 Scarborough RM, Huang W, Pandey A, Bauer SM, Zhang X, Jia ZJ. WO2005032488, 2005
    PubMed
  • 17 Magnus NA, Confalone PN, Storace L, Patel M, Wood CC, Davis WP, Parsons JrR. L. J. Org. Chem. 2003; 68: 754
    CrossrefPubMedSearch in Google Scholar
  • 18 General Procedure: Synthesis of QuinazolinedionesTo a round-bottom flask was added 2-(benzylamino)benzoic acid 2 (1.0 mmol) as a solid, α-chloroaldoxime O-methanesulfonate 1 (1.2 mmol), K3PO4 (3.0 mmol), DMAP (0.5 mmol), and t-BuOH (5.0 mL). Then H2O (2.0 mmol) was added to the reaction mixture. The reaction mixture was allowed to stir at room temperature for 15–18 h. After completion of reaction, the reaction mixture was quenched with sat. NH4Cl and extracted with EtOAc. The combined organic layers were washed with sat. NaCl (brine), dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography (4:1, hexanes/EtOAc) to provide the corresponding quinazolinedione.
  • 19 Analytical Data for 1-Benzyl-3-phenylquinazoline-2,4(1H,3H)-dione (3a)Prepared according to general procedure from N-(methylsulfonyloxy)benzimidoyl chloride (1a) and 2-(benzylamino)benzoic acid (2a) yielding 3a in 242.81 mg (74 %) as a white solid. 1H NMR (300 MHz, CDCl3): δ = 8.31 (d, J = 7.8 Hz, 1 H), 7.65–7.47 (m, 4 H), 7.42–7.24 (m, 9 H), 5.44 (s, 2 H). 13C NMR (75 MHz, CDCl3): δ = 161.9, 151.6, 140.3, 135.6, 129.4, 129.0, 128.8, 128.5, 127.8, 127.1, 123.5, 115.9, 114.9, 47.6. IR (thin film): ν = 1704, 1656, 1349, 1317, 1330, 760, 702, 691, 672 cm–1. HRMS (ESI-TOF): m/z [M + Na]+ calcd for C21H16N2O2Na: 351.1104; found: 351.1105.
  • 20 Analytical Data for 1-Benzyl-3-(4-nitrophenyl)quinazoline-2,4(1H,3H)-dione (3b)Prepared according to general procedure from N-(methylsulfonyloxy)-4-nitrobenzimidoyl chloride (1b) and 2-(benzylamino)benzoic acid (2a) yielding 3b in 305.95 mg (82 %) as a white solid. 1H NMR (300 MHz, CDCl3): δ = 8.33 (d, J = 8.7 Hz, 2 H), 8.20 (dd, J = 8.1, 1.5 Hz, 1 H), 7.59 (t, J = 1.8 Hz, 1 H), 7.48 (d, J = 9.0 Hz, 2 H), 7.33–7.16 (m, 7 H), 5.34 (s, 2 H). 13C NMR (75 MHz, CDCl3): δ = 161.4, 150.9, 147.7, 141.2, 140.2, 136.0, 135.2, 130.1, 129.4, 129.1, 128.0, 126.7, 126.4, 124.6, 123.7, 115.8, 114.9, 113.4, 47.6. IR (thin film): ν = 1704 1663 1344 1310 1478 860 752 699 688 cm–1. HRMS (ESI-TOF): m/z [M + H]+ calcd for C21H16N3O4: 374.1135; found: 374.1136.