# Aqueous glyoxal: a versatile synthon in heterocyclic synthesis

**Authors:** Abolfazl Olyaei, Mahdieh Sadeghpour

PMC · DOI: 10.1039/d5ra08496b · RSC Advances · 2026-02-19

## TL;DR

This review explores how aqueous glyoxal can be used to create a wide variety of complex organic molecules, especially heterocycles, through different chemical strategies.

## Contribution

The paper provides a comprehensive overview of aqueous glyoxal's role in synthesizing diverse molecular frameworks using one-pot and multicomponent methods.

## Key findings

- Aqueous glyoxal can form five- and six-membered heterocycles through addition and condensation reactions.
- It is effective in creating aromatic compounds, fused heterocycles, and polycyclic systems using various catalysts.
- The review highlights one-pot and multicomponent reaction strategies for efficient synthesis.

## Abstract

Glyoxal is a versatile, non-volatile compound with a wide range of applications, attracting significant interest from both researchers and various industries. It can be synthesized by numerous methods and is potentially derivable from natural sources. Moreover, glyoxal forms various hydrates and oligomers (e.g., dimers and trimers). Its high reactivity allows it to undergo addition, condensation, and crosslinking reactions with a wide range of compounds, including alcohols, amines, aldehydes, carboxylic acids, cellulose, polyvinyl alcohol, and urea. This review discusses the applications of aqueous glyoxal as a versatile reagent in organic synthesis, with a focus on protocols for generating diverse molecular frameworks, including five- and six-membered heterocycles, aromatic compounds, fused heterocycles, polyaza polycyclic compounds, polyoxa polycyclic compounds and polyaza–polyoxa polycyclic compounds. The employed strategies include one-pot, multicomponent reactions and sequential methods, which use different catalysts under various conditions.

This review highlights the applications of aqueous glyoxal as a versatile reagent in organic synthesis, with a focus on protocols for generating diverse molecular frameworks, including five- and six-membered heterocycles.

## Linked entities

- **Chemicals:** glyoxal (PubChem CID 7860), aldehydes (PubChem CID 6449839), urea (PubChem CID 1176)

## Full-text entities

- **Diseases:** cancer (MESH:D009369), cytotoxic (MESH:D064420), sarcoma (MESH:D012509)
- **Chemicals:** ammonium (MESH:D064751), polyvinyl alcohol (MESH:D011142), nickel (MESH:D009532), p-chlorophenol (MESH:C029107), ethylene glycol (MESH:D019855), thiols (MESH:D013438), thiophenol (MESH:C042983), H3PW12O40 (MESH:C519880), toluene (MESH:D014050), isopropylamine (MESH:C035263), 1,2,4-triazole (MESH:C045575), ethylene (MESH:C036216), lactic acid (MESH:D019344), carbazole (MESH:C041514), 2-aminopyrazine (MESH:C079424), CO (MESH:D002248), amino acids (MESH:D000596), CH2Cl2 (MESH:D008752), MgSO4 (MESH:D008278), azide (MESH:D001386), carboxylic acid (MESH:D002264), Etidronic acid (MESH:D012968), nitrogen (MESH:D009584), quinoxalines (MESH:D011810), urea (MESH:D014508), benzofurans (MESH:D001572), imidazolidin-2-one (MESH:C004916), naphthols (MESH:D009284), NH4Cl (MESH:D000643), H3PO4 (MESH:C030242), ZnCl2 (MESH:C016837), acetal (MESH:D000080), phenols (MESH:D010636), benzoxazine (MESH:D048588), phenylalanine (MESH:D010649), hydrazine monohydrate (MESH:C029424), Cl (MESH:D002713), tannin (MESH:D013634), 1,2-propanediol (MESH:D019946), amine (MESH:D000588), l-(+)-tartaric acid (MESH:C029768), triethylamine (MESH:C016162), esters (MESH:D004952), CH3CN (MESH:C032159), alanine (MESH:D000409), 1,5-diphenylcarbazide (MESH:D004160), 2-amino-2-methyl-1-propanol (MESH:C006551), 1,4,8,11-tetraazacyclotetradecane (MESH:C024560), carbohydrates (MESH:D002241), methylmalonic acid (MESH:D008764), nitramine (MESH:C015384), allylamine (MESH:D000499), C (MESH:D002244), 1,2-dihydronaphtho[2,1-b]furans (MESH:C584628), acetylene (MESH:D000114), methylamine (MESH:C027451), imidazoline (MESH:D048288), p-toluenesulfonamide (MESH:C025417), N,N'-dimethylurea (MESH:C018275), 1,2,4-triazine (MESH:C093444)
- **Species:** Staphylococcus aureus (species) [taxon 1280], Rattus norvegicus (brown rat, species) [taxon 10116], Mus musculus (house mouse, species) [taxon 10090]
- **Mutations:** C) for 15, C for 5-11, C for 1-2, C in 5-10, T74D, C for 25-70, C for 5-60
- **Cell lines:** A549 — Homo sapiens (Human), Lung adenocarcinoma, Cancer cell line (CVCL_0023), U937 — Homo sapiens (Human), Adult acute monocytic leukemia, Cancer cell line (CVCL_0007), Jurkat — Homo sapiens (Human), Childhood T acute lymphoblastic leukemia, Cancer cell line (CVCL_0065), K562 — Homo sapiens (Human), Blast phase chronic myelogenous leukemia, BCR-ABL1 positive, Cancer cell line (CVCL_0004), A2780 — Homo sapiens (Human), Ovarian endometrioid adenocarcinoma, Cancer cell line (CVCL_0134)

## Full text

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## Figures

130 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12917490/full.md

## References

168 references — full list in the complete paper: https://tomesphere.com/paper/PMC12917490/full.md

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Source: https://tomesphere.com/paper/PMC12917490