# Eco-Friendly Synthesis of 2-Styryl-benzo[d][1,3]oxazin-4-ones from N-Cinnamoyl-Anthranilic Acids

**Authors:** Armando Zarrelli, Luigi Longobardo

PMC · DOI: 10.3390/molecules31040709 · Molecules · 2026-02-18

## TL;DR

This paper presents a green, efficient method to synthesize 2-styryl-benzo[d][1,3]oxazin-4-ones from N-cinnamoyl-anthranilic acids using eco-friendly solvents and no metal catalysts.

## Contribution

A novel, metal-free, and chromatography-free synthesis method for 2-styryl-benzo[d][1,3]oxazin-4-ones using green chemistry principles.

## Key findings

- N-cinnamoyl anthranilic acids are synthesized efficiently using the mixed carbonic anhydride method.
- The final products are obtained without the need for chromatographic purification.
- The method uses green solvents and avoids metal catalysts and reflux conditions.

## Abstract

N-cinnamoyl anthranilic acids are synthesized in a single, eco-friendly step by condensing various cinnamic acids with free 2-aminobenzoic acid derivatives using the mixed carbonic anhydride method. Subsequently, converting the resulting N-cinnamoyl anthranilic acids into their corresponding mixed carbonic anhydrides rapidly and efficiently affords 2-styryl-benzo[d][1,3]oxazin-4-ones. The method employs green solvents, such as acetone and 2-methyltetrahydrofuran; does not require metal catalysts or reflux conditions; and yields the desired final products without chromatographic purification.

## Linked entities

- **Chemicals:** 2-aminobenzoic acid (PubChem CID 227), acetone (PubChem CID 180), 2-methyltetrahydrofuran (PubChem CID 7301)

## Full-text entities

- **Diseases:** obesity (MESH:D009765), injury to (MESH:D014947), inflammatory (MESH:D007249)
- **Chemicals:** anhydride (MESH:D000812), amide (MESH:D000577), Piperonylic Acid (MESH:C005455), phenol (MESH:D019800), palladium (MESH:D010165), benzene (MESH:D001554), water (MESH:D014867), petroleum ether (MESH:C004544), Cinnamic Acids (MESH:C029010), isobutyl chloroformate (MESH:C039311), 3,4-dimethoxycinnamic acid (MESH:C065784), 13C (MESH:C000615229), ethyl chloroformate (MESH:C007658), methanol (MESH:D000432), Carbonate (MESH:D002254), metal (MESH:D008670), silica gel (MESH:D058428), Aromatic amino acids (MESH:D024322), quinazolinones (MESH:D052999), 2-methyltetrahydrofuran (MESH:C550584), N2 (MESH:D009584), 2-aminobenzamide (MESH:C000219), benzoic acid (MESH:D019817), HCA (MESH:D003373), carbon (MESH:D002244), ester (MESH:D004952), triethylamine (MESH:C016162), benzoxazinone (MESH:D048588), citric acid (MESH:D019343), carbonic anhydride (MESH:D002245), morpholine (MESH:C037574), quinazolines (MESH:D011799), anthranilic acids (MESH:D062367), alcohols (MESH:D000438), Caffeic Acid (MESH:C040048), isocyanides (MESH:D003486), avenanthramides (MESH:C514463), 2-aminobenzoic acid (MESH:C031385), ethyl ether (MESH:D004986), oxazine (MESH:D010078), 2-(benzo[d][1,3]dioxol-5-yl)-6-methoxy-4H-benzo[d][1,3]oxazin-4-one (-), ethyl acetate (MESH:C007650), aluminum (MESH:D000535), cetilistat (MESH:C520092), Hexane (MESH:D006586), pyridine (MESH:C023666), benzodiazepines (MESH:D001569), alpha-amino acid (MESH:D000596), Na2SO4 (MESH:C012036), acetone (MESH:D000096), phenols (MESH:D010636), amine (MESH:D000588)
- **Species:** Homo sapiens (human, species) [taxon 9606]

## Full text

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## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12943305/full.md

## References

22 references — full list in the complete paper: https://tomesphere.com/paper/PMC12943305/full.md

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Source: https://tomesphere.com/paper/PMC12943305