Reaction between isocyanides and dialkyl acetylenedicarboxylates in the presence of strong CH-acids: one-pot synthesis of highly functionalized annulated 4H-pyrans
“…All the reactions are clean, and the products were obtained in good to high yields within 35–60 min at ambient temperature. Structures of all the products were confirmed by comparison of their spectroscopic as well as physical data with those of the authentic samples prepared from the previously reported methods …”
“…All the reactions are clean, and the products were obtained in good to high yields within 35–60 min at ambient temperature. Structures of all the products were confirmed by comparison of their spectroscopic as well as physical data with those of the authentic samples prepared from the previously reported methods …”
“…Subsequent [1 þ 4] cycloaddition reaction with isocyanide 2 affords an iminolactone intermediate 7 [27,28], followed by reaction with alcohol leads to the vinylogous carbonate 8. Subsequently loss of acetone from 8 and the reaction with another molecule of alcohol to afford product 5 (Scheme 1) [24].…”
“…The structures of the compounds 6a-c and 6e were deduced by spectroscopic analysis and comparison of their spectroscopic data with those reported in the literature. 14 The physical and spectral data for compound 6d are given in the Experimental section.…”
Section: Methodsmentioning
confidence: 99%
“…E-mail: nasiri@uma.ac.ir solvents and usually the time of the reactions was long. [13][14][15][16][17] In continuation of our interest in the generation and trapping of various zwitterionic species by H-acids, [18][19][20] we wish to report the one-pot reaction between cyclic 1,3-dicarbonyl compounds and dialkyl acetylene dicarboxylates in the presence of TosMIC in PEG to produce new highly functionalised 2-amino-4Hpyrans in good to high yields.…”
The reaction of cyclic CH-acids such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 4-hydroxy-6methyl-2H-pyran-2-one, or 4-hydroxycumarin with dialkyl acetylene dicarboxylates in the presence of tosylmethyl isocyanide (TosMIC) in polyethylene glycol (PEG-300) leads to new annulated highly functionalised 2-amino-4Hpyrans at room temperature in good yields.
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