Superacid-catalyzed tandem Meyer-Schuster rearrangement/intramolecular hydroamination of o-anilinopropargyl alcohols for the synthesis of 2,3-dihydro-4(1H)-quinolones

被引：9

作者：

Sun, Guofeng ^{[1
]}

Cheng, Fengkai ^{[1
]}

Tao, Ruiheng ^{[1
]}

Sun, Yuxing ^{[1
]}

Pan, Jinpeng ^{[1
]}

Zhu, Yaohua ^{[1
]}

Wang, Zhonghua ^{[1
]}

Wu, Fanhong ^{[1
]}

Yin, Yan ^{[1
,2
]}

机构：

[1] Shanghai Inst Technol, Sch Chem & Environm Engn, 100 Hai Quan Rd, Shanghai 201418, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2016年 / 46卷 / 15期

基金：

中国国家自然科学基金;

关键词：

2; 3-Dihydro-4(1H)-quinolones; hydroamination reaction; Meyer-Schuster rearrangement; o-anilinopropargyl alcohols; superacid; INTRAMOLECULAR HYDROAMINATION; TETRAHYDROQUINOLINES; REARRANGEMENT; SULFONAMIDES; DERIVATIVES; CYCLIZATION; SERIES;

D O I：

10.1080/00397911.2016.1196293

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A TfOH-catalyzed synthesis of 2,3-dihydro-4(1H)-quinolones from o-anilinopropargyl alcohols was developed. Studies of N-protecting groups and substituents in phenyl rings showed that diverse groups could be applied. By controlling the catalyst loading, o-anilinopropargyl alcohols underwent the expected transformation smoothly to produce N-protected or N-deprotected 2,3-dihydro-4 (1H)-quinolones in good yields. This transformation probably involved a tandem Meyer-Schuster rearrangement/intramolecular hydroamination reaction process. [GRAPHICS] .

引用

页码：1249 / 1256

页数：8

共 50 条

[41] A facile synthesis of 2,3-dihydro-2-aryl-4(1H)-quinazolinones catalyzed by scandium(III) triflate
Chen, Jiu Xi
Wu, Hua Yue
Su, Wei Ke
CHINESE CHEMICAL LETTERS, 2007, 18 (05) : 536 - 538
[42] Synthesis of thiazino- and thiazoloquinazolinones by cyclization of S-(2-propenyl) derivatives of 2-thioxo-2,3-dihydro-4(1H)-quinazolinone
Orysyck, VV
Zborovskii, YL
Staninets, VL
Dobosh, AA
Khripak, SM
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2003, (05): : 739 - 744
[43] Synthesis of Thiazino- and Thiazoloquinazolinones by Cyclization of S-(2-Propenyl) Derivatives of 2-Thioxo-2,3-dihydro-4(1H)-quinazolinone
V. V. Orysyk
Yu. L. Zborovskii
V. I. Staninets
A. A. Dobosh
S. M. Khripak
Chemistry of Heterocyclic Compounds, 2003, 39 (5) : 640 - 644
[44] AGENTS ACTING ON THE CENTRAL NERVOUS-SYSTEM .37. SYNTHESIS OF 1-TOSYL-3-SUBSTITUTED-AMINOMETHYLENE-6(OR 7)-METHOXY-2,3-DIHYDRO-4(1H)-QUINOLONES
SANGWAN, NK
RASTOGI, SN
ANAND, N
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1979, 17 (06): : 653 - 655
[45] Synthesis of (±)-2-aryl- and (±)-2-alkyl-substituted 2,3-dihydro-4(1H)-quinazolinones from 2-nitro- and 2-aminobenzamide
Bunce, Richard A.
Nammalwar, Baskar
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[46] [bmim]HSO4: an efficient and reusable catalyst for one-pot three-component synthesis of 2,3-dihydro-4(1H)-quinazolinones
Darvatkar, Nitin B.
Bhilare, Sachin V.
Deorukhkar, Amol R.
Raut, Dilip G.
Salunkhe, Manikrao M.
GREEN CHEMISTRY LETTERS AND REVIEWS, 2010, 3 (04) : 301 - 306
[47] One-Pot, Three-Component Synthesis of 2,3-Dihydro-4(1H)-Quinazolinones Catalyzed by Perchlorated Zirconia (HClO4/ZrO2) Nanoparticles as a Solid Acid Catalyst
Zeinab Hamidi
Mohammad Abdollahi-Alibeik
Seyed Yousef Mosavian
Silicon, 2018, 10 : 2491 - 2497
[48] One-Pot, Three-Component Synthesis of 2,3-Dihydro-4(1H)-Quinazolinones Catalyzed by Perchlorated Zirconia (HClO4/ZrO2) Nanoparticles as a Solid Acid Catalyst
Hamidi, Zeinab
Abdollahi-Alibeik, Mohammad
Mosavian, Seyed Yousef
SILICON, 2018, 10 (06) : 2491 - 2497
[49] A novel approach to 2-arylmethyl-2,3-dihydro-4(1H)-quinazolinones. Total synthesis of the alkaloids glycozolone-A and glycozolone-B
Klassmueller, Thomas
Tringali, Claudia
Bracher, Franz
NATURAL PRODUCT RESEARCH, 2024, 38 (01) : 119 - 127
[50] SYNTHESIS OF 1,2-DIHYDROPYRIDINES, 2,3-DIHYDRO-4(1H)-PYRIDINONE, AND 1,2,3,4-TETRAHYDROPYRIDINES VIA N-ACYL N,O-HEMIACETAL FORMATION
RODUIT, JP
WYLER, H
HELVETICA CHIMICA ACTA, 1985, 68 (02) : 403 - 414

← 1 2 3 4 5 →