KOtBu-Catalyzed Synthesis of Isoindole Derivatives from N-Benzyl Amides Bearing an Ortho Alkynyl Group via 1,2-Acyl Shift

被引:0
作者
Shimazumi, Ryoma [1 ]
Morimoto, Moe [1 ]
Tobisu, Mamoru [1 ,2 ]
机构
[1] Osaka Univ, Grad Sch Engn, Dept Appl Chem, Osaka 5650871, Japan
[2] Osaka Univ, Inst Open & Transdisciplinary Res Initiat ICS OTRI, Innovat Catalysis Sci Div, Osaka 5650871, Japan
关键词
CYCLIZATION; CHEMISTRY;
D O I
10.1021/acs.orglett.4c02055
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In this study, we present the catalytic conversion of benzylamides featuring an ortho alkynyl moiety into 1-acylisoindole derivatives via a 1,2-acyl shift. Remarkably, this transformation proceeds without the need for transition-metal catalysts; instead, (KOBu)-Bu-t alone serves as the catalyst. This method enables the efficient synthesis of isoindoles from easily accessible amides with an atom economy of 100%.
引用
收藏
页码:5587 / 5591
页数:5
相关论文
共 26 条
[1]  
Bonnett R., 1981, Advances in Heterocyclic Chemistry, V29, P341, DOI DOI 10.1016/S0065-2725(08)60790-4
[2]   Metal-free entry to phosphonylated isoindoles by a cascade of 5-exo-dig cyclization, a [1,3]-alkyl shift, and aromatization under microwave heating [J].
Dieltiens, Nicolai ;
Stevens, Christian V. .
ORGANIC LETTERS, 2007, 9 (03) :465-468
[3]   Synthesis of isoindol-1-ylphosphonate derivatives via Pd(0)-catalyzed reaction of α-amino (2-alkynylphenyl) methylphosphonate with aryl iodide [J].
Ding, Qiuping ;
Wang, Bing ;
Wu, Jie .
TETRAHEDRON LETTERS, 2007, 48 (49) :8599-8602
[4]   Selective synthesis of 2,3-disubstituted-2H-isoindol-1-ylphosphonate and 2,3-disubstituted-1,2-dihydroiso-quinolin-1-ylphosphonate via metal-tuned reaction of α-amino (2-alkynylphenyl)methylphosphonate [J].
Ding, Qiuping ;
Ye, Yang ;
Fan, Renhua ;
Wu, Jie .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5439-5442
[5]   Aryne Cycloaddition with Stable Munchnones: Synthesis of 9,10-Dihydro-9,10-epiminoanthracenes and Isoindoles [J].
Fang, Yuesi ;
Larock, Richard C. ;
Shi, Feng .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 3 (01) :55-57
[6]   Transition-Metal-Catalyzed p-Bond-Assisted C-H Bond Functionalization: An Emerging Trend in Organic Synthesis [J].
Gandeepan, Parthasarathy ;
Cheng, Chien-Hong .
CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (04) :824-838
[7]   Novel N→C acyl migration reaction of acyclic imides:: A facile method for α-aminoketones and β-aminoalcohols [J].
Hara, O ;
Ito, M ;
Hamada, Y .
TETRAHEDRON LETTERS, 1998, 39 (31) :5537-5540
[8]   Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles [J].
Heugebaert, Thomas S. A. ;
Roman, Bart I. ;
Stevens, Christian V. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (17) :5626-5640
[9]   Gold(III) Chloride Catalyzed Synthesis of 1-Cyanoisoindoles [J].
Heugebaert, Thomas S. A. ;
Stevens, Christian V. .
ORGANIC LETTERS, 2009, 11 (21) :5018-5021
[10]   Nickel-Catalyzed Addition of C-C Bonds of Amides to Strained Alkenes: The 1,2-Carboaminocarbonylation Reaction [J].
Ito, Yuri ;
Nakatani, Syun ;
Shiraki, Ryota ;
Kodama, Takuya ;
Tobisu, Mamoru .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (02) :662-666