Collect. Czech. Chem. Commun.
1988, 53, 1519-1528
https://doi.org/10.1135/cccc19881519
A general method of preparation of N-diformylmethylazoles and cycloimonium diformyl methylides
Vladimír Krála, Viktor Vladimirovich Semenovb, Mikhail Ivanovich Kanishchevb, Zdeněk Arnolda, Svyatoslav Arkadievich Shevelevb and Albert Aleksandrovich Fainzilbergb
a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow B-334, U.S.S.R.
Abstract
Formylation of easily accessible heteroarylacetic acids (R-CH2COOH, R = imidazole, pyrazole, tetrazole, pyridine) afforded in high yields the corresponding trimethinium salts R-C(=CH-N(CH3)2)CH=N(CH3)2)n+ nX- which on alkaline hydrolysis were converted into N-diformylmethylazoles R-C(CHO)=CH-OH. Their quaternization gave cycloimonium diformyl methylides.
