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Diels-alder reactions with inverse electron demand. II. The reaction of benzamidine with π-deficient heteroaromatic compounds.

✍ Scribed by H.P. Figeys; A. Mathy

Publisher
Elsevier Science
Year
1981
Tongue
French
Weight
228 KB
Volume
22
Category
Article
ISSN
0040-4039

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✦ Synopsis

Benzamidine (I) reacts with several s-tetrazines to give as-triazines in moderate to good yield, together with some s-triazines; separate experiments have shown that these are due to the fact that (I) also undergoes Diels-Alderreactions with as-and even with s-triazines. Although the so-called "Diels-Alder reaction with inverse electron demand" of various a-deficient heteroaromatic compounds with electron-rich triple and double carbon-carbon bonds is a well-documented field (2) , very few reactions of this type have been described where the dienophile is an open-chain C=N double bond, suitably activated by -alectron-donating substituents(3). Imidates react with 3,6-dimethoxycarbonyl-s-tetrazine (DMCT) at 60' (dioxane) to give

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