Nitriles in organic synthesis: The reaction of trichloroacetonitrile with active methylene reagents (original) (raw)
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Molecules, 2009
Phenacylmalononitrile 1 reacts with dimethylformamide dimethyl acetal to yield an enaminone which could be readily converted into a pyrrole or an aminopyridazine by treating with ammonium acetate and hydrazine hydrate, respectively. Compound 1 reacted with hydrazine hydrate in ethanol at room temperature to yield the dihydropyridazine 9 as a single product. In refluxing ethanol this product further reacted with hydrazine hydrate to yield the novel dihydropyrazolopyridazinamine 10.
Zeitschrift für Naturforschung B, 1986
3-Thiocyanatomethyl C innam onitrile, R eductive Cleavage, Pyrrole Derivatives /3-Thiocyanatomethyl cinnam onitrile derivatives coupled with aromatic diazonium salts to afford the corresponding azo com pounds, which undergo reductive cyclization into pyrrole derivatives. The utility of organic cyano com pounds in heterocyclic synthesis has recently received consider able attention [1, 2], Our group has been involved in the last years in a program aiming to develop effi cient procedures for synthesis of polyfunctionally substituted azoles [3, 4], azines [5, 6 ] and their con densed derivatives [7, 8 ] utilizing simple and readily obtainable polyfunctionally substituted nitriles. D u ring this phase of our research we could show that whereas ethylidenem alononitrile derivative l a does not couple with aromatic diazonium salts, the pre sence o f cyano substituent on the methyl m oiety (as in lb ) sufficiently activates the adjacent m ethylene group for coupling [9], The resulting hydrazones could be utilized for synthesis of pyridazine-6 -imine derivatives [10]. It seem ed to us of value to see if the presence of other functional substituent on the methyl m oiety in 1 can effect similar activation.
ChemInform, 2011
A practical and efficient process has been developed for the synthesis of 1-substituted 4-acyl-1H-1,2,3triazoles using a three-step one-pot synthetic approach. This transformation involves an initial preparation of triisopropylsilyl (TIPS)-protected ynones from acid chlorides and TIPS-acetylene, followed by a AgF-mediated TIPS deprotection and Cu-catalyzed Huisgen cycloaddition. The increased chemical stability of TIPS-protected ynones was an important factor in the high overall product yield.