1393371-28-2Relevant articles and documents
Base-catalysed [3 + 2] cycloaddition of propargylamines and aldehydes to substituted furans
Shen, Jinhai,Zhao, Jing,Hu, Bing,Chen, Yangxin,Wu, Longqiao,You, Qihua,Zhao, Li
, p. 600 - 603 (2018/02/14)
A base-catalysed [3 + 2] cycloaddition reaction of propargylamines and aldehydes for the regiospecific synthesis of substituted furans under metal-free conditions is developed. Propargylamines are used as allenyl anion equivalents and applied in [3 + 2] cycloaddition reactions with aldehydes. Various substituted furans are provided up to 91% yield for 28 examples.
Bronsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans
Mothe, Srinivasa Reddy,Lauw, Sherman Jun Liang,Kothandaraman, Prasath,Chan, Philip Wai Hong
, p. 6937 - 6947 (2012/10/07)
A Bronsted acid-catalyzed method to prepare tri- and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH?H 2O-mediated tandem alkylation/cycloisomerization of the propargylic 1,4-diol with the β-dicarbonyl compound was found to selectively occur to provide the tetrasubstituted furan product. On the other hand, increasing the reaction temperature to 80 °C was discovered to result in preferential p-TsOH?H2O-catalyzed dehydrative rearrangement of the unsaturated alcohol and formation of the 2,3,5-trisubstituted furan adduct.
