A novel cycloaddition reaction of 4-bromo-2,6-dimethyl-phenylisonitrile with acetylene derivatives

1,8-Diazafloren-9-one with alkyl and aryl isocyanides in the presence of acetylenic esters: A facile synthesis of γ-spiroiminolactones

“…The characteristic signal due to the spiro carbon was described at δ 91.66 and the carbon of the C=N group resonated at δ 158.07. The 1 H and 13 C NMR spectra of 4a-h are similar to those of 4a, except for isocyanide, ester residues.…”

One-pot, three component reactions between isocyanides and dialkyl acetylenedicarboxylates in the presence of phenyl isocyanate: synthesis of dialkyl 2-(alkyl/arylimino)-2,5-dihydro-5-oxo-1-phenyl-1H-pyrrole-3,4-dicarboxylate

“…[6][7] The reactivity of nucleophilic carbenes such as isocyanides towards dimethyl acetylenedicarboxylate (DMAD) is well documented. [8][9][10] The reaction of isocyanides with carbon-carbon triple bonds occurs in a stepwise manner through a zwitterionic intermediate, the ultimate fate of which appears to be dictated by the nature of original triple-bonded substrate. [11][12][13][14][15][16][17][18][19] In continuation of our interest in the application of isocyanides in heterocyclic synthesis, [20][21][22][23][24][25][26][27] we now report the reaction between alkyl/aryl isocyanides 1 and dialkyl acetylenedicarboxylate 2 in the presence of phenyl isocyanate.…”

Reaction between Alkyl Isocyanides and Dialkyl Acetylenedicarboxylates in the Presence of 1-aryl-2-thiocyanatoethanone Yields Highly Functionalised Iminolactones

“…1,2 The reactivity of nucleophilic carbenes, such as isocyanides, towards dimethyl acetylenedicarboxylate (DMAD) is well documented. 3,4 The reaction of isocyanides with carbon-carbon triple bonds occurs in a stepwise manner through a zwitterionic intermediate, the ultimate fate of which appears to be dictated by the nature of the original triple-bonded substrate. [4][5][6] many synthetic protocols for the synthesis of iminolactones have been reported.…”

“…3,4 The reaction of isocyanides with carbon-carbon triple bonds occurs in a stepwise manner through a zwitterionic intermediate, the ultimate fate of which appears to be dictated by the nature of the original triple-bonded substrate. [4][5][6] many synthetic protocols for the synthesis of iminolactones have been reported. [7][8][9][10][11][12][13][14][15][16][17][18][19] The most widely used approach to iminolactones synthesis is the isocyanide-based reactions.…”