Metal- and solvent-free domino reaction of 2-isocyanophenol esters to benzoxazines: long-range 1,5-acyl migration on 1,4-diazabutatriene

被引：1

作者：

Akbari, Alireza ^{[1
]}

Khosravi, Hormoz ^{[1
]}

Bauer, Felix ^{[2
]}

Rominger, Frank ^{[3
]}

Breit, Bernhard ^{[2
]}

Balalaie, Saeed ^{[1
]}

机构：

[1] KN Toosi Univ Technol, Peptide Chem Res Inst, Dept Chem, POB 15875-4416, Tehran, Iran

[2] Albert Ludwigs Univ Freiburg, Inst Organ Chem, Albertstr 21, D-79104 Freiburg, Germany

[3] Heidelberg Univ, Organ Chem Inst, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

来源：

CHEMICAL COMMUNICATIONS | 2024年 / 60卷 / 41期

基金：

美国国家科学基金会;

关键词：

MULTICOMPONENT REACTIONS; ISOCYANIDES;

D O I：

10.1039/d4cc01214c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first example of intramolecular nucleophilic addition of 1,4-diazabutatriene to ester is disclosed. This approach provides a facile and versatile synthesis for functionalized 2H-1,4-benzoxazines under metal-, reagent-, and solvent-free conditions. Experimental and computational studies revealed the pivotal role of 1,5-acyl migration as the self-catalytic step in the reaction selectivity. The first example of intramolecular nucleophilic addition of 1,4-diazabutatriene to esters is disclosed. This approach provides a facile and versatile synthesis for functionalized 2H-1,4-benzoxazines through metal-, reagent-, and solvent-free conditions.

引用

页码：5451 / 5454

页数：4

共 2 条

[1] Platinum-Catalyzed Tandem Cycloisomerization Reaction of Benzoendiynyl Esters: Regioselective Long-Range 1,5-Acyl Migration
Chen, Zhiyuan
Jia, Xuegong
Huang, Jiapian
Yuan, Jianjun
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (21): : 10674 - 10681
[2] Sulfur Catalyzed Metal- and Solvent-Free ABB'C Four-Component Synthesis of N-Arylidene-2-aryl-imidazo[1-2-a]azin-3-amines via Strecker Reaction
Pavithra, Thangavel
Devi, E. Sankari
Nagarajan, Subbiah
Sridharan, Vellaisamy
Maheswari, C. Uma
CHEMISTRYSELECT, 2021, 6 (14): : 3548 - 3552

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