Synthesis of Tetracyclic Benzoxazolo-indol-3-ones from Isatogens and Arynes through a [3+2]-Cycloaddition and Skeletal Reorganization

被引：0
作者：
Halnor, Swapnil V. [1 ,2 ]
Singh, Maneesha [1 ,2 ]
Dhote, Pawan S. [1 ,2 ]
Ramana, Chepuri V. [1 ,2 ]
机构：
[1] CSIR Natl Chem Lab, Div Organ Chem, Pune 411008, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 20期
关键词：
IN-SITU GENERATION; ONE-POT SYNTHESIS; CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITION; SELECTIVE SYNTHESIS; MODULAR SYNTHESIS; FACILE SYNTHESIS; N-ARYLATION; DERIVATIVES; EFFICIENT;
D O I：
10.1021/acs.joc.4c01667
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The construction of an unprecedented tetracyclic benzoxazolo-indol-3-one scaffold has been executed through the [3 + 2]-cycloaddition of isatogens with arynes. The initially formed benzisoxazolo-indol-3-one intermediate undergoes a skeletal reorganization through a 1,3-sigmatropic shift/retro-Mannich reaction with the net formation of one C-N and two C-O bonds. The Lewis acid-catalyzed allylation of some of the resulting benzoxazolo-indol-3-ones resulted in oxazepino-indolones with promising photophysical properties.
引用
收藏
页码：14919 / 14928
页数：10
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