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Beilstein J Org Chem. 2013 Nov 4;9:2344-53. doi: 10.3762/bjoc.9.269. eCollection 2013.
A convenient and efficient methodology for the synthesis of densely substituted pyrrole-fused isocoumarins, which employs solid-supported silica sulfuric acid (SSA) as catalyst, has been developed. When the mixture of ninhydrin adducts of acetylacetone/ethyl acetoacetate and primary amines was heated on the solid surface of SSA under solvent-free conditions, the pyrrole-fused isocoumarins were formed in good yields. This synthetic method has several advantages such as the employment of solvent-free reaction conditions without the use of any toxic reagents and metal catalysts, the ease of product isolation, the use of a recyclable catalyst, the low cost, the easy availability of the starting materials, and the excellent yields of products.
已开发出一种方便、高效的方法,用于合成稠取代的吡咯并异香豆素,该方法采用负载型硅胶硫酸(SSA)作为催化剂。当无溶剂条件下将乙酰丙酮/乙酰乙酸乙酯的缩合产物与伯胺的混合物加热到 SSA 的固体表面时,吡咯并异香豆素可以高产率形成。这种合成方法具有许多优点,例如采用无溶剂反应条件,无需使用任何有毒试剂和金属催化剂,产物易于分离,使用可回收催化剂,成本低,起始原料易得,产物收率高。