One-Pot Synthesis of O-Allylhydroxylamines through the Organocatalytic Oxidation of Tertiary Allylic Amines Followed by a [2,3]-Meisenheimer Rearrangement

被引：28

作者：

Theodorou, Alexis ^{[1
]}

Limnios, Dimitris ^{[1
]}

Kokotos, Christoforos G. ^{[1
]}

机构：

[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 13期

关键词：

alcohols; green chemistry; organocatalysis; oxidation; rearrangement; MEISENHEIMER REARRANGEMENT; N-OXIDES; ENANTIOSELECTIVE SYNTHESIS; CHIRALITY TRANSFER; AZETOPYRIDOINDOLES; DERIVATIVES; EPOXIDATION; ACID; 2,2,2-TRIFLUOROACETOPHENONE; 12-CARBAEUDISTOMIN;

D O I：

10.1002/chem.201406173

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A cheap, green, and highly efficient one-pot method for the synthesis of O-protected allylic alcohols is described. By utilizing 2,2,2-trifluoroacetophenone as the organocatalyst and H2O2 as the oxidant, a variety of allylic amine N-oxides were synthesized, which upon heating are converted to the final products through a [2,3]-Meisenheimer rearrangement.

引用

页码：5238 / 5241

页数：4

共 50 条

[31] One-pot synthesis of 2-oxa-7-azaspiro[4.4]nonane-8,9-diones using Mn(III)-based oxidation of 4-acylpyrrolidine-2,3-diones
Thanh-Truc Huynh
Van-Ha Nguyen
Nishino, Hiroshi
TETRAHEDRON LETTERS, 2017, 58 (37) : 3619 - 3622
[32] One-Pot Synthesis of Quinazolin-4(3H)-ones through Anodic Oxidation and the Related Mechanistic Studies
Cao, Liu
Huo, Hengrui
Zeng, Haipeng
Yu, Yu
Lu, Dengfu
Gong, Yuefa
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4764 - 4773
[33] A practical and versatile approach toward a one-pot synthesis of 2,3-disubstituted 4(3H)-quinazolinones
Dabiri, Minoo
Salehi, Peyman
Bahramnejad, Mahboobeh
Alizadeh, Mohsen
MONATSHEFTE FUR CHEMIE, 2010, 141 (08): : 877 - 881
[34] Efficient one-pot synthesis of 2,3-dihydroquinazoline-4(1H)-ones promoted by FeCl3/neutral Al2O3
Wu, Suo Juan
Zhao, Zi Qiang
Gao, Jing Shuo
Chen, Bao Hua
Chen, Guo Feng
RESEARCH ON CHEMICAL INTERMEDIATES, 2019, 45 (04) : 2327 - 2339
[35] Convenient "on-water" one-pot, synthesis of flavonols catalyzed by LiOH.H2O- and H2O2-mediated oxidation
Kumar, Sumit
Ambatwar, Ramesh
Gupta, Vaibhav
Khatik, Gopal L.
RESEARCH ON CHEMICAL INTERMEDIATES, 2023, 49 (03) : 901 - 915
[36] Ni-Al2O3 as reusable heterogeneous catalyst for expedient one-pot synthesis of naphthopyrans
Kalita, Subarna Jyoti
Saikia, Nilakhy
Deka, Dibakar Chandra
Mecadon, Hormi
RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (09) : 6863 - 6871
[37] A green one-pot synthesis of 3(5)-substituted 1,2,4-triazol-5(3)-amines as potential antimicrobial agents
Beyzaei, Hamid
Khosravi, Zahra
Aryan, Reza
Ghasemi, Behzad
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (12) : 2565 - 2573
[38] One-pot synthesis of C/Bi/Bi2O3 composite with enhanced photocatalytic activity
Hao, Qiang
Wang, Ruiting
Lu, Haojie
Xie, Ci'an
Ao, Weihua
Chen, Daimei
Ma, Chao
Yao, Wenqing
Zhu, Yongfa
APPLIED CATALYSIS B-ENVIRONMENTAL, 2017, 219 : 63 - 72
[39] One-Pot Four-Component Synthesis of Thieno[2,3-d]pyrimidin-4-amines via Sequential Gewald/Cyclocondensation Reactions
Adib, Mehdi
Janatian Ghazvini, Helia
Soheilizad, Mehdi
Saeedi, Sara
Tajbakhsh, Mahmood
Amanlou, Massoud
HELVETICA CHIMICA ACTA, 2015, 98 (08) : 1079 - 1086
[40] One-Pot Synthesis of Pyrrolo[3,4-a]indolizine-1,3-diones through [3+2] Cycloaddition-Oxidation Reaction Catalyzed by CuII Salt and O2 as the Oxidant
Liu, Yun
Hu, Hua-You
Su, Xian-Bin
Sun, Jin-Wei
Cao, Chang-Sheng
Shi, Yan-Hui
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (10) : 2020 - 2026

← 1 2 3 4 5 →