Synthesis 2022; 54(13): 3085-3092
DOI: 10.1055/s-0041-1737414
paper

Rapid and Facile Synthesis of Isomaleimides: Dehydration of Maleamic Acids using Methanesulfonyl Chloride

Khyarul Alam
,
Elvis C. McFee
,
This research was supported by the National Science Foundation (CAREER­ CHE-1351883) and the College of Arts & Sciences at the University of North Carolina at Greensboro.


Abstract

The dehydration of maleamic acids using methanesulfonyl chloride as a dehydrating agent to selectively and rapidly (<15 min) generate isomaleimides is reported. A variety of maleamic acid derivatives produce the corresponding isomaleimides in good to excellent yields. Adaptation of this protocol under flow synthesis allows for similar efficiency and decreased reaction times (13 seconds residence time). It was also possible to convert maleic anhydride into the desired isomaleimide in a two-step, one-flask operation.

Supporting Information



Publication History

Received: 27 January 2022

Accepted after revision: 28 February 2022

Article published online:
07 April 2022

© 2022. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Meldal M, Diness F. Trends Chem. 2020; 2: 569
    • 1b Haldón E, Nicasio MC, Pérez PJ. Org. Biomol. Chem. 2015; 13: 9528
    • 1c Thirumurugan P, Matosiuk D, Jozwiak K. Chem. Rev. 2013; 113: 4905
  • 2 Bonandi E, Christodoulou MS, Fumagalli G, Perdicchia D, Rastelli G, Passarella D. Drug Discovery Today 2017; 22: 1572
    • 3a Tsou K.-C, Barrnett RJ, Seligman AM. J. Am. Chem. Soc. 1955; 77: 4613
    • 3b Ezzell SA, Hansen RG, Anderson GJ. PCT Int. Appl WO 020832 A1, 1997
    • 3c Harwood HJ, Pyriadi TM. J. Org. Chem. 1971; 36: 821
    • 3d Curtin DY, Miller LL. J. Am. Chem. Soc. 1967; 89: 637
    • 3e Cotter RJ, Sauers CK, Whelan JM. J. Org. Chem. 1961; 26: 10
    • 3f Oishi T, Fujimoto M, Yoshimoto N, Kimura T. Polym. J. 1989; 21: 655
    • 4a Kirino O, Rubin B, Casida JE. Agric. Biol. Chem. 2014; 49: 267
    • 4b Conley NR, Hung RJ, Willson CG. J. Org. Chem. 2005; 70: 4553
    • 4c Fruk L, Graham D. Heterocycles 2003; 60: 2305
    • 4d Nielsen O, Buchardt O. Synthesis 1991; 819
    • 4e Corrie JE. T, Moore MH, Wilson GD. J. Chem. Soc., Perkin Trans. 1 1996; 777
    • 5a Joseph-Nathan P, Mendoza V, García E. Can. J. Chem. 1974; 52: 129
    • 5b Rubinstein H, Parnarouskis M, Feuer H. J. Org. Chem. 1973; 38: 2166
    • 5c Narita M, Akiyama M, Okawara M. Bull. Chem. Soc. Jpn. 1971; 44: 437
    • 6a Dolci E, Froidevaux V, Joly-Duhamel C, Auvergne R, Boutevin B, Caillol S. Polym. Rev. 2016; 56: 512
    • 6b Nanda T, Ravikumar PC. Org. Lett. 2020; 22: 1368
    • 6c Li X.-R, Chen S.-Q, Fan J, Li C.-J, Wang X, Liu Z.-W, Shi X.-Y. Org. Lett. 2020; 22: 8808
    • 6d Uno BE, Deibler KK, Villa C, Raghuraman A, Scheidt KA. Adv. Synth. Catal. 2018; 360: 1719
    • 6e Ravasco JM. J. M, Faustino H, Trindade A, Gois PM. P. Chem. Eur. J. 2018; 25: 43
    • 6f Cunha S, Rodovalho W, Azevedo NR, Mendonça M. dO, Lariucci C, Vencato I. J. Braz. Chem. Soc. 2002; 13: 629
    • 7a Anderson NH, Ollis WD, Thorpe JE, Ward AD. J. Chem. Soc., Perkin Trans. 1 1975; 825
    • 7b Guevara JA, Trujillo JG, Quintana D, Jiménez HA, Arellano MG, Bahena JR, Tamay F, Ciprés FJ. Med. Chem. Res. 2018; 27: 989
    • 7c Sarannya V, Rishwana SS, Mahalakshmy R, Mahendran AR, Surender R, Vijayakumar CT. J. Elastomers Plast. 2019; 52: 495
    • 8a Klimenkovs I, Bakis E, Priksane A. Synth. Commun. 2013; 43: 2634
    • 8b Haval KP, Mhaske SB, Argade NP. Tetrahedron 2006; 62: 937
    • 8c Isobe T, Ishikawa T. J. Org. Chem. 1999; 64: 6989
    • 9a Al-Huniti MH, Perez MA, Garr MK, Croatt MP. Org. Lett. 2018; 20: 7375
    • 9b Deiab G. aI. A, Al-Huniti MH, Hyatt IF. D, Nagy EE, Gettys KE, Sayed SS, Joliat CM, Daniel PE, Vummalaneni RM, Morehead AT, Sargent AL, Croatt MP. Beilstein J. Org. Chem. 2017; 13: 384
    • 10a Kurita K, Suzuki Y, Enari T, Kikuchi M, Nishimura SI, Ishii S. J. Polym. Sci., Part A: Polym. Chem. 1994; 32: 393
    • 10b Shield Wallace J, Tan L.-S, Arnold FE. Polymer 1990; 31: 2411
  • 11 Burness DM, Wilson BD. US 3232763, 1966
  • 12 Kozyrev AN, Zheng G, Lazarou E, Dougherty TJ, Smith KM, Pandey RK. Tetrahedron Lett. 1997; 38: 3335
    • 13a Byrne FP, Jin S, Paggiola G, Petchey TH. M, Clark JH, Farmer TJ, Hunt AJ, McElroy CR, Sherwood J. Sustainable Chem. Processes 2016; 4: 7
    • 13b Capello C, Fischer U, Hungerbühler K. Green Chem. 2007; 9: 927
  • 14 Webb D, Jamison TF. Org. Lett. 2011; 14: 568
  • 15 Guirado A, Zapata A, Ramírez de Arellano MC. Tetrahedron 1997; 53: 5305
  • 16 Jha A, Duffield KM, Ness MR, Ravoori S, Andrews G, Bhullar KS, Rupasinghe HP. V, Balzarini J. Bioorg. Med. Chem. 2015; 23: 6404