Construction of Diverse Fused Chromene Frameworks via Isocyanide-Based Three-Component Reaction

作者：Yu‐Wei He, Li Huang, Kun Huang, Chao‐Guo Yan, Jing Sun, Ying Han · 发表于：The Journal of Organic Chemistry · 年份：2024 · DOI：10.1021/acs.joc.4c01142 · 被引用次数：12 · 研究领域：Multicomponent Synthesis of Heterocycles、Synthesis and biological activity、Synthesis of Organic Compounds

A convenient synthetic protocol for diverse fused chromenes was successfully developed by a three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and various cyclic 1,3-dipolarophiles containing o -hydroxyphenyl group. In the absence of any catalyst, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 3-( o -hydroxyarylidene)indolin-2-ones in tetrahydrofuran at 60 °C resulted in unique functionalized spiro[cyclobuta[ c ]chromene-1,3′-indolines] in good yields and with high diastereoselectivity. However, the similar three-component reaction with 2-(5-halo-2-hydroxyarylidene)indolin-2-ones afforded unexpected chain products in satisfactory yields. In addition, the three-component reaction of alkyl isocyanides, dialkyl but-2-ynedioates, and 2-( o -hydroxyarylidene)-1,3-indanediones in tetrahydrofuran at 60 °C resulted in complex indeno[2′,1′:5,6]pyrano[3,4- c ]chromene derivatives in high yields and with high diastereoselectivity.