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Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

ABSTRACT: The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine (3) are reported. The electron-deficient nature of 3 permits rapid cycloaddition with a variety of electron-rich dienophiles, including amidines, enamines, enol ethers, ynamines, and ketene acetals in high to moderate yields. 1H NMR studies of a representative cycloaddition reaction between 3 and an amidine revealed a remarkable reaction rate and efficiency (1 mM, <60 s, CD3CN, 23 °C, >95%).

SUBMITTER: Glinkerman CM

PROVIDER: S-EPMC5935562 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

Glinkerman Christopher M CM Boger Dale L DL

Organic letters 20180416 9

The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine (3) are reported. The electron-deficient nature of 3 permits rapid cycloaddition with a variety of electron-rich dienophiles, including amidines, enamines, enol ethers, ynamines, and ketene acetals in high to moderate yields. <sup>1</sup>H NMR studies of a representative cycloaddition reaction between 3 and an amidine revealed a remarkable reaction rate and efficiency (1 mM, <60 s, CD<sub>3</sub ...[more]

PMID: 29659291

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