# Investigation for the easy and efficient synthesis of 1H-benzo[d][1,3]oxazine-2,4-diones

**Authors:** Nikolaos Mitsostergios, Vasileios Athanasopoulos, Spyridon Mourtas

PMC · DOI: 10.1039/d5ra04014k · RSC Advances · 2025-08-04

## TL;DR

This paper presents a simple and efficient two-step method to synthesize 1H-benzo[d][1,3]oxazine-2,4-diones from 2-aminobenzoic acids.

## Contribution

The novel contribution is a streamlined synthetic route using specific carbonyloxy groups and thionyl chloride for efficient compound formation.

## Key findings

- A two-step synthesis method was successfully developed for 1H-benzo[d][1,3]oxazine-2,4-diones.
- The use of Fmoc, Cbz, and EtOCO groups as carbonyloxy sources proved effective.
- Thionyl chloride effectively promoted activation, cyclization, and compound formation.

## Abstract

We investigated a two-step approach for the easy and efficient synthesis of 1H-benzo[d][1,3]oxazine-2,4-diones starting from 2-aminobenzoic acids, using the urethane type fluorenylmethyloxycarbonyl (Fmoc), benzyloxycarbonyl (Cbz) and ethyloxycarbonyl (EtOCO) groups as the source of carbonyloxy group, and thionyl chloride to promote activation, cyclization and 1H-benzo[d][1,3]oxazine-2,4-diones formation.

We report the synthesis of 1H-benzo[d][1,3]oxazine-2,4-diones from 2-aminobenzoic acids, using fluorenylmethyloxycarbonyl (Fmoc), benzyloxycarbonyl (Cbz) and ethyloxycarbonyl (EtOCO) groups as the source of carbonyloxy group, and thionyl chloride.

## Linked entities

- **Chemicals:** thionyl chloride (PubChem CID 24386)

## Full-text entities

- **Genes:** BCHE (butyrylcholinesterase) [NCBI Gene 590] {aka BCHED, CHE1, CHE2, E1}
- **Chemicals:** 2-Aminobenzoic acid (MESH:C031385), DEE (MESH:D004986), phthalimide (MESH:C037431), 13C (MESH:C000615229), 3H (MESH:D014316), sodium hydroxide (MESH:D012972), THF (MESH:C018674), urethane (MESH:D014520), isatoic anhydride (MESH:C037902), indoline-2,3-dione (MESH:C572590), isatin (MESH:D007510), EtCl (MESH:D005018), acetone (MESH:D000096), Cbz (MESH:D002220), sodium hypochlorite (MESH:D012973), carboxylic acid (MESH:D002264), thionyl chloride (MESH:C023589), TFA (MESH:D014269), 2H (MESH:D003903), AcOH (-), phosgene (MESH:D010705), HCl (MESH:D006851), Acetonitrile (MESH:C032159), NaHCO3 (MESH:D017693), silica gel (MESH:D058428), Pd (MESH:D010165), 7a (MESH:C040548), ethylene (MESH:C036216), oxygen (MESH:D010100), ethyl chloroformate (MESH:C007658), peroxides (MESH:D010545), Na2SO4 (MESH:C012036), carbamate (MESH:D002219), LiBr (MESH:C040949), H (MESH:D006859), dioxane (MESH:C025223), C15H13NO4 (MESH:C067652), N-(9-fluorenylmethoxycarbonyloxy) succinimide (MESH:C490223), benzyl chloroformate (MESH:C018241), methaqualone (MESH:D008702), chloride (MESH:D002712), o-aminobenzoic acid (MESH:D062367), LiCl (MESH:D018021), carbon dioxide (MESH:D002245), oxalyl chloride (MESH:C092266), Hex (MESH:D006586), benzyl chloride (MESH:C021292), 4-quinazolinone (MESH:C061339), ethyl acetate (MESH:C007650), Na2CO3 (MESH:C005686), phthalic anhydride (MESH:C043103), H2O (MESH:D014867)
- **Species:** hepatitis C virus [taxon 11103]
- **Cell lines:** S24A — Mus musculus (Mouse), Hybridoma (CVCL_B5AU)

## Full text

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## Figures

8 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12320480/full.md

## References

36 references — full list in the complete paper: https://tomesphere.com/paper/PMC12320480/full.md

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Source: https://tomesphere.com/paper/PMC12320480