1978
DOI: 10.1021/jo00414a006
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Synthesis of some 2-aminofurans from cyanoacetone enolate and their rearrangement to 3-cyanopyrroles with ammonia

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Cited by 32 publications
(7 citation statements)
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“…Phenacyl cyanides 311 [ 579 , 580 , 581 , 582 , 583 , 584 , 585 , 586 , 587 , 588 , 589 , 590 ] and phenacyl thiocyanates 312 [ 591 , 592 , 593 , 594 , 595 ] have been proven to be valuable tools for the synthesis of a wide variety of heterocyclic compounds. They are simply prepared via the reaction of α-haloketones with alkali metal cyanides and thiocyanates, respectively (Eq 7).…”
Section: Miscellaneous Reactions Of α-Haloketonesmentioning
confidence: 99%
“…Phenacyl cyanides 311 [ 579 , 580 , 581 , 582 , 583 , 584 , 585 , 586 , 587 , 588 , 589 , 590 ] and phenacyl thiocyanates 312 [ 591 , 592 , 593 , 594 , 595 ] have been proven to be valuable tools for the synthesis of a wide variety of heterocyclic compounds. They are simply prepared via the reaction of α-haloketones with alkali metal cyanides and thiocyanates, respectively (Eq 7).…”
Section: Miscellaneous Reactions Of α-Haloketonesmentioning
confidence: 99%
“…Previously we have shown that generated o-quinones attacked by b-diketones, barbituric acid, thiobarbituric acid and 4-hydroxycoumarin to produce new functionalized benzofuranes, spiropyrimidines, dispirothiopyrimidines and cumestanes derivatives, respectively [5][6][7][8]. Among the carbon centered nucleophiles, methyl cyanoacetates and cyanoacetone, have received considerable attention [9][10][11][12][13]. The reaction adducts often undergo further reactions such as Knovenagel reaction or electrophilic reaction of nitrile group [2,[14][15][16].…”
Section: Introductionmentioning
confidence: 99%
“…The reaction adducts often undergo further reactions such as Knovenagel reaction or electrophilic reaction of nitrile group [2,[14][15][16]. To the best of our knowledge there are few reports about nucleophilic reaction of their enolic hydroxy group [13]. The purpose of this work is to perform a kinetic and mechanistic study of the electrochemical oxidation of catechols in the presence of cyanoacetone and methyl cyanoacetate in the same condition as other C-nucleophiles.…”
Section: Introductionmentioning
confidence: 99%
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“…Phenacyl cyanides 311 [579][580][581][582][583][584][585][586][587][588][589][590] and phenacyl thiocyanates 312 [591][592][593][594][595] have been proven to be valuable tools for the synthesis of a wide variety of heterocyclic compounds. They are simply prepared via the reaction of α-haloketones with alkali metal cyanides and thiocyanates, respectively (Eq 7).…”
Section: A Cyanation and Thiocyanationmentioning
confidence: 99%