Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2025 Mar 14:21:596-600.
doi: 10.3762/bjoc.21.46. eCollection 2025.

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

Wei-Jin Chang  1 , Sook Yee Liew  2 , Thomas Kurz  3 , Siow-Ping Tan  1
Affiliations

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

Wei-Jin Chang et al. Beilstein J Org Chem. .

Abstract

The hydantoin scaffold is renowned for its wide-ranging biological activities, including antibacterial, antiviral, anticancer, anti-inflammatory, and anticonvulsant effects. In this study, we present an innovative, sustainable approach to synthesizing hydantoins (H2a-j) directly from amino acids. This method employs a column chromatography-free, two-step, one-pot microwave-assisted synthesis that delivers hydantoins in yields ranging from 34% to 89%. The protocol demonstrates exceptional functional group tolerance, accommodating phenyl, aliphatic, phenol, alcohol, heterocyclic, and sulfide groups. This scalable, rapid, and eco-friendly strategy offers a promising avenue for the efficient synthesis of hydantoins, aligning with green chemistry principles and expanding the accessibility of these bioactive compounds for pharmaceutical applications.

Keywords: Urech synthesis; amino acids; hydantoin; microwave-assisted; one-pot reaction.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
N-Carbamylation of ʟ-phenylaniline using KOCN in water.
Scheme 2
Scheme 2
One-pot microwave-assisted synthesis of hydantoins from amino acids.
Figure 1
Figure 1
Hydantoins (H2a–j) synthesized from the one-pot procedure. The hydantoins were characterized using 1H and 13C NMR and HRMS.
See this image and copyright information in PMC

References

    1. Khodair A I, Metwally A I, Kheder N A, El–Tahawy M M T. J Mol Struct. 2024;1303:137565. doi: 10.1016/j.molstruc.2024.137565. - DOI
    1. Chen L, Hao Y, Song H, Liu Y, Li Y, Zhang J, Wang Q. J Agric Food Chem. 2020;68:10618–10625. doi: 10.1021/acs.jafc.0c04488. - DOI - PubMed
    1. Shankaraiah N, Nekkanti S, Chudasama K J, Senwar K R, Sharma P, Jeengar M K, Naidu V G M, Srinivasulu V, Srinivasulu G, Kamal A. Bioorg Med Chem Lett. 2014;24:5413–5417. doi: 10.1016/j.bmcl.2014.10.038. - DOI - PubMed
    1. Lin X, Tago K, Okazaki N, So T, Takahashi K, Mashino T, Tamura H, Funakoshi-Tago M. Int Immunopharmacol. 2021;100:108092. doi: 10.1016/j.intimp.2021.108092. - DOI - PubMed
    1. Wolf H H, Swinyard E A, Goodman L S. J Pharm Sci. 1962;51(1):74–76. doi: 10.1002/jps.2600510114. - DOI - PubMed

LinkOut - more resources