A mild and efficient CAN mediated oxidation of Morita–Baylis–Hillman adducts of 5-methyl-N-alkylisatin to 5-formyl-N-alkylisatin
摘要:
A simple, mild and efficient CAN mediated oxidation of Morita-Baylis-Hillman adducts of 5-methyl-N-alkylisatins 1a-13a to 5-formyl-N-alkylisatins lb-13b under ambient reaction conditions is reported. Simple and isomerized 5-methyl-N-alkylisatin derivatives 1-4 have also been tested and failed to provide the corresponding formylated products. A plausible reaction mechanism has been proposed. (C) 2008 Elsevier Ltd. All rights reserved.
Synthesis of Highly Functionalized
Allene-Appended Oxindoles and 2-Oxo-1,2-dihydroindol-3-ylidene-2,5-dihydrofurans via
Claisen Rearrangement and Cyclization
Synthesis of highly functionalized allene appended oxin-dole derivatives from vinyl propargyl ether derivatives of Morita― Baylis―Hillman adducts of isatin via Claisen rearrangement has been achieved. Synthetic utility of the allene derivatives obtained has been demonstrated with the synthesis of methyl 2,5-dihydro-5-methyl-2-(1-methyl-2-oxoindolin-3-ylidene)furan-3-carboxylates in a one-pot cyclization
Convenient Synthetic Protocols for Diverse Functionalized Dihydrobenzofuran-Fused Spiro-indanedione-oxindole Scaffolds
作者:Jing Sun、Xueyan Liu、Qiu Sun、Ying Han、Chao-Guo Yan
DOI:10.1021/acs.joc.3c00887
日期:2023.8.18
1′-cyclopenta[b]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-(o-hydroxybenzylidene)-1,3-indanediones selectively, resulting in spiro[cyclopropa[c]chromene-1,2′-indene]-1′,3′-diones or dispiro[indene-2,1′-cyclopenta[b]benzofuran-2′,3″’-indolines]
通过靛红和 2-(邻羟基亚苄基)-1,3-茚满二酮的 Morita-Baylis-Hillman (MBH) 碳酸酯的碱促进环化反应,方便地合成了多种功能化的二氢苯并呋喃螺环-茚满二酮-羟吲哚支架。以DABCO或DMAP为基础促进剂,可以选择性合成两个非对映体二螺[茚-2,1'-环戊[ b ]苯并呋喃-2',3"'-二氢吲哚]。更重要的是,DABCO或DMAP选择性地促进靛红和2-(邻羟基亚苄基)-1,3-茚二酮的MBH甲酸酯的成环反应,产生螺[环丙[ c ]色烯-1,2'-茚]-1 ',3'-二酮或二螺[茚-2,1'-环戊[ b ]苯并呋喃-2',3"'-二氢吲哚]。此外,与靛红的 MBH 马来酰亚胺进行类似反应,得到二螺[茚-2,5'-苯并呋喃[2',3':1,5]环戊[1,2- c ]吡咯-4',3"'-二氢吲哚] 高产率和高非对映选择性。
Regioselective and Diastereoselective Construction of Diverse Dispiro-Indanone-Fluorenone-Oxindole Motifs
作者:Dan Liu、Jing Sun、Ying Han、Chao-Guo Yan
DOI:10.1021/acs.joc.3c02047
日期:2023.12.15
A convenient synthetic protocol for regioselective and diastereoselective construction of complex dispiro-indanone-fluorenone-oxindole motifs was developed by the base-promoted annulation reaction of bindone and MBH carbonates of isatins by adjusting reaction conditions. DABCO promoted the annulation reaction of bindone and MBH carbonates of isatins in DCM at room temperature, affording dispiro[indene-2
Synthesis of Spiro[indoline-pyridine]-dicarboxylates and Substituted Alkylidene Oxindoles by Azomethine Ylides and MBH Carbonates of Isatins
作者:Daqian Wang、Ting Tang、Jing Sun、Ying Han、Chao-Guo Yan
DOI:10.1021/acs.orglett.4c01236
日期:2024.5.17
developed an efficient protocol for the synthesis of spiro[indoline-pyridine]dicarboxylates and substituted alkylidene oxindoles through [3 + 3] cycloaddition and Michael addition individually by azomethine ylides and various MBH carbonates of isatins. The selective generation of cyclic products and chain products was achieved by changing the substituents at the 3-position of the oxindoles. The features