Synthesis of 1,2,3-Triazine Derivatives by Deoxygenation of 1,2,3-Triazine 1‑Oxides

A convenient, efficient, and inexpensive method has been developed for the synthesis of 1,2,3-triazine derivatives via deoxygenation of 1,2,3-triazine 1-oxide using trialkyl phosphites. Triethyl phosphite is more reactive than trimethyl phosphite, and both phosphites form their corresponding phospha...

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Bibliographic Details
Published in:Organic letters 2022-09, Vol.24 (36), p.6543-6547
Main Authors: Rivera, Gildardo, De Angelis, Luca, Al-Sayyed, Ammar, Biswas, Soumen, Arman, Hadi, Doyle, Michael P.
Format: Article
Language:English
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Summary:A convenient, efficient, and inexpensive method has been developed for the synthesis of 1,2,3-triazine derivatives via deoxygenation of 1,2,3-triazine 1-oxide using trialkyl phosphites. Triethyl phosphite is more reactive than trimethyl phosphite, and both phosphites form their corresponding phosphates in these reactions. This procedure provides a range of aromatic and aliphatic substituted 1,2,3-triazine-4-carboxylate derivatives cleanly in high yields. Unexpected 1,2,4-triazine derivatives were also obtained as minor products during deoxygenation of 1,2,3-triazine-4-carboxylate 1-oxides having an aliphatic substituent at the 5-position.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02484