2016
DOI: 10.1016/j.tet.2016.08.084
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Regioisomeric synthesis of dihydrofuro[2,3-d]pyrimidines in a diastereoselective manner involving nitrogen ylides in one-pot three-component reaction

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Cited by 15 publications
(5 citation statements)
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“…The reaction was further accelerated by microwaves. 36 Recently, a regioisomeric synthesis of some highly functionalized dihydrofuro [2,3-d]pyrimidines from one-pot three-component reaction of barbituric acids, aryl aldehydes, and pyridinium bromides in the presence of triethylamine as a base was introduced by Bhuyan et al 37 During the reaction, nitrogen ylides were formed and involved in [4 +1] annulation as well as [2 +1] annulation processes in which the two regioisomeric compounds were produced after intramolecular ring transformation. Diastereoselective synthesis of dihydrofurocoumarin via a three-component reaction of aldehyde, pyridinium salt, and 4-hydroxycoumarin in an aqueous medium was reported by An et al 38 They noted that this method avoids excessive use of pyridine and trimethylamine catalysts.…”
Section: Introductionmentioning
confidence: 99%
“…The reaction was further accelerated by microwaves. 36 Recently, a regioisomeric synthesis of some highly functionalized dihydrofuro [2,3-d]pyrimidines from one-pot three-component reaction of barbituric acids, aryl aldehydes, and pyridinium bromides in the presence of triethylamine as a base was introduced by Bhuyan et al 37 During the reaction, nitrogen ylides were formed and involved in [4 +1] annulation as well as [2 +1] annulation processes in which the two regioisomeric compounds were produced after intramolecular ring transformation. Diastereoselective synthesis of dihydrofurocoumarin via a three-component reaction of aldehyde, pyridinium salt, and 4-hydroxycoumarin in an aqueous medium was reported by An et al 38 They noted that this method avoids excessive use of pyridine and trimethylamine catalysts.…”
Section: Introductionmentioning
confidence: 99%
“…In 2016, Dutta and colleagues [128] reported a diastereoselective method for the synthesis of dihydrofuro[2,3‐ d ]pyrimidines 162 , 163 through a one‐pot, three‐component reaction involving nitrogen ylides. The researchers discovered that employing acetonitrile as a solvent and 1.2 mmol of triethylamine as a base resulted in the highest yield of the two products ( 162 and 163 ) in a shorter time frame.…”
Section: Synthetic Techniques For the Preparation Of Furo[23‐d]pyrimi...mentioning
confidence: 99%
“…In path I, the intermediate 78 produced the compound 74 by a direct cyclization process via eliminating pyridine. But in path II, first, intermediate 79 with the cyclopropane ring was formed, which underwent an intramolecular ring transformation, and proceeded through the intermediates 80 and 81 in the presence of base to produce the product 75 [46].…”
Section: Synthesis Of Dihydrofuro[23‐d]pyrimidinesmentioning
confidence: 99%
“…In 2013, Lee and co-workers developed the rhodium(II)-catalyzed reactions of cyclic diazo compounds derived from thiobarbituric acid or barbituric acid with styrenes and arylacetylenes for the synthesis furo [2,3-d] 80 and 81 in the presence of base to produce the product 75 [46].…”
Section: Synthesis Of Dihydrofuro [23-d]pyrimidinesmentioning
confidence: 99%