Sun Jing, Liu Xueyan, Sun Qiu, Han Ying, Yan Chao-Guo
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China.
J Org Chem. 2023 Aug 18;88(16):11562-11580. doi: 10.1021/acs.joc.3c00887. Epub 2023 Jul 27.
Diverse functionalized dihydrobenzofuran spiro-indanedione-oxindole scaffolds were conveniently synthesized by base-promoted cyclization reaction of Morita-Baylis-Hillman (MBH) carbonates of isatins and 2-(-hydroxybenzylidene)-1,3-indanediones. The two diastereomeric dispiro[indene-2,1'-cyclopenta[]benzofuran-2',3″'-indolines] could be selectively synthesized by using DABCO or DMAP as a base promoter. More importantly, DABCO or DMAP facilitated the annulation reaction of MBH formates of isatins and 2-(-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[]chromene-1,2'-indene]-1',3'-diones or dispiro[indene-2,1'-cyclopenta[]benzofuran-2',3″'-indolines]. Additionally, a similar reaction with MBH maleimides of isatins afforded dispiro[indene-2,5'-benzofuro[2',3':1,5]cyclopenta[1,2-]pyrrole-4',3″'-indolines] in high yields and with high diastereoselectivity.
通过异吲哚酮的森田-贝利斯-希尔曼（MBH）碳酸酯与2-（-羟基亚苄基）-1,3-茚二酮的碱促进环化反应，方便地合成了多种功能化的二氢苯并呋喃螺茚二酮-氧化吲哚支架。使用1,4-二氮杂双环[2.2.2]辛烷（DABCO）或4-二甲氨基吡啶（DMAP）作为碱促进剂，可以选择性地合成两种非对映异构的二螺[茚-2,1'-环戊[a]苯并呋喃-2',3″'-吲哚啉]。更重要的是，DABCO或DMAP选择性地促进了异吲哚酮的MBH甲酸酯与2-（-羟基亚苄基）-1,3-茚二酮的环化反应，生成螺[环丙烷[a]色烯-1,2'-茚]-1',3'-二酮或二螺[茚-2,1'-环戊[a]苯并呋喃-2',3″'-吲哚啉]。此外，异吲哚酮的MBH马来酰亚胺的类似反应以高产率和高非对映选择性得到二螺[茚-2,5'-苯并呋喃[二氢苯并呋喃螺茚二酮-氧化吲哚支架。使用1,4-二氮杂双环[2.2.2]辛烷（DABCO）或4-二甲氨基吡啶（DMAP）作为碱促进剂，可以选择性地合成两种非对映异构的二螺[茚-2,1'-环戊[a]苯并呋喃-2',3″'-吲哚啉]。更重要的是，DABCO或DMAP选择性地促进了异吲哚酮的MBH甲酸酯与2-（-羟基亚苄基）-1,3-茚二酮的环化反应，生成螺[环丙烷[a]色烯-1,2'-茚]-1',3'-二酮或二螺[茚-2,1'-环戊[a]苯并呋喃-2',3″'-吲哚啉]。此外，异吲哚酮的MBH马来酰亚胺的类似反应以高产率和高非对映选择性得到二螺[茚-2,5'-苯并呋喃[2',3':1,5]环戊[1,2-b]吡咯-4',3″'-吲哚啉]。 2',3':1,5]环戊[1,2-b]吡咯-4',3″'-吲哚啉]。 2',3':1,5]环戊[1,2-b]吡咯-4',3″'-吲哚啉]。
你提供的原文中存在一些格式和重复等问题，译文已尽量准确翻译，但原文可能需要进一步优化表述以便更清晰理解。
Zotero 插件