Synthesis of functionalized 5-imino-2,5-dihydro-furans through the reaction of isocyanides with activated acetylenes in the presence of ethyl bromopyruvate.
The reaction between alkyl(aryl) isocyanides and dibenzoylacetylene in the presence of ethyl bromopyruvate leads to ethyl 3,4-dibenzoyl-2-bromomethyl-5-alkyl(aryl)imino-2,5-dihydro-furan-2-carboxylates in high yields. Dialkyl acetylenedicarboxylates react with tert-butyl isocyanide and ethyl bromopyruvate to produce 3,4-dialkyl 2-ethyl 2-bromomethyl-5-tert-butylimino-2,5-dihydro-furan-2,3,4-tricarboxylates.
Yavari
Issa
I
Department of Chemistry, Tarbiat Modarres University, Tehran, Iran.yavarisa@modares.ac.ir
Hossaini
Zinatossadat
Z
Sabbaghan
Maryam
M
D000480:Alkynes / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011773:Pyruvates / Q000737:chemistry; D019289:Pyruvic Acid / Q000737:chemistry
D000480:Alkynes; D003486:Cyanides; D005663:Furans; D011773:Pyruvates; C017092:bromopyruvate; D019289:Pyruvic Acid