Functionalization of 4-(Diethoxyphosphoryl)-4,7-dihydro5H-thiopyrano[3,4-b]furan-5-carboxylic Acid Ester at the α-Position of the Furan Fragment
L. M. Pevznera, *, A. A. Ostrovskayaa, M. L. Petrova, and A. V. Stepakova, b
aSt. Petersburg State Institute of Technology (Technical University), St. Petersburg, 190013 Russia
bSaint Petersburg State University, St. Petersburg, 198504 Russia
email: *pevzner_lm@list.ru
Received 5 May, 2022
Abstract—
On an example of aminomethylation, chloromethylation, and acetylation reactions, it was shown that ethyl 4-(diethoxyphosphoryl)-4,7-dihydro-5H-thiopyrano[3,4-b]furan-5-carboxylate selectively enters the electrophilic substitution reactions at the position 2. The interaction of the obtained 2-chloromethyl derivative with O-, S- and N-nucleophiles was studied. Based on the 2-acetyl derivative, a 4-substituted 1,2,3-thiadiazole ring was formed under the conditions of the Hurd–Mori reaction.
Keywords:
4,7-dihydro-5Н-thiopyrano[3,4-b]furan,
electrophilic substitution reactions,
О,S,N-nucleophiles,
2-chloromethyl-4,7-dihydro-5Н-thiopyrano[3,4-b]furan,
1,2,3-thiadiazole,
Hurd–Mori reaction
DOI: 10.1134/S1070363222100073