Reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of bidentate nucleophiles.
The reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of 1,2-ethanediol leads to N (1)-(alkyl)-2-(5,7-dioxo-1,4-dioxepane-6-yl)-2-methylpropanamides. 1,3-Propanediol or 1,4-butanediol produce hydroxyalkyl 1-(tert-butyl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxylates. When the reaction was performed in the presence of catechol, bis(2-hydroxyphenyl) 2-[2-(tert-butylamino)-1,1-dimethyl-2-oxoethyl]malonate was obtained. 2-Aminophenols react with alkyl isocyanides in the presence of isopropylidene Meldrum's acid to produce 1-alkyl-N (3)-(2-hydroxyaryl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxamides in good yields.
Yavari
Issa
I
Department of Chemistry, Tarbiat Modarres University, Tehran, Iran. yavarisa@modares.ac.ir
Sabbaghan
Maryam
M
Hossaini
Zinatossadat
Z
D000577:Amides / Q000138:chemical synthesis; D002072:Butylene Glycols / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003486:Cyanides / Q000737:chemistry*; D019855:Ethylene Glycol / Q000737:chemistry; D006018:Glycols / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis
D000577:Amides; D002072:Butylene Glycols; D002396:Catechols; D003486:Cyanides; D006018:Glycols; D011409:Propylene Glycols; D011759:Pyrrolidines; C041787:1,3-propanediol; C039681:1,4-butanediol; D019855:Ethylene Glycol; C034221:catechol