Asymmetric, Three-Component, One-Pot Synthesis of Spiropyrazolones and 2,5-Chromenediones from Aldol Condensation/NHC-Catalyzed Annulation Reactions

被引：57

作者：

Wang, Lei ^{[1
]}

Li, Sun ^{[1
]}

Chauhan, Pankaj ^{[1
]}

Hack, Daniel ^{[1
]}

Philipps, Arne R. ^{[1
]}

Puttreddy, Rakesh ^{[2
]}

Rissanen, Kari ^{[2
]}

Raabe, Gerhard ^{[1
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Univ Jyvaskyla, Nanosci Ctr, Dept Chem, Jyu 40014, Finland

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 15期

关键词：

asymmetric synthesis; chromenedione; multicomponent reaction; N-heterocyclic carbene; spiropyrazolone; N-HETEROCYCLIC CARBENES; ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; BRONSTED ACID; ACTIVATION; ORGANOCATALYSIS; PYRAZOLONES; DERIVATIVES; PROGRESS; KETONES;

D O I：

10.1002/chem.201600515

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel one-pot, three-component diastereo- and enantioselective synthesis of spiropyrazolones has been developed involving the aldol condensation of an enal to generate ,-unsaturated pyrazolones, which react with a second equivalent of enal through an N-heterocyclic carbene (NHC)-catalyzed [3+2] annulation. The desired spirocyclopentane pyrazolones are obtained in moderate to good yields and good to excellent stereoselectivities. Alternatively, starting from cyclic 1,3-diketones, 2,5-chromenediones are available through [2+4] annulation.

引用

页码：5123 / 5127

页数：5

共 50 条

[21] One-pot three-component synthesis of β-acetamido carbonyl compounds catalyzed by heteropoly acids
Javid, Ali
Heravi, Majid M.
Bamoharram, Fatemeh F.
MONATSHEFTE FUR CHEMIE, 2012, 143 (05): : 831 - 834
[22] One-pot three-component synthesis of β-acetamido carbonyl compounds catalyzed by heteropoly acids
Ali Javid
Majid M. Heravi
Fatemeh F. Bamoharram
Monatshefte für Chemie - Chemical Monthly, 2012, 143 : 831 - 834
[23] Nickel chloride-catalyzed one-pot three-component synthesis of pyrazolophthalazinyl spirooxindoles
Zhang, Xiao-Nan
Li, Yong-Xiao
Zhang, Zhan-Hui
TETRAHEDRON, 2011, 67 (38) : 7426 - 7430
[24] EDTA-catalyzed synthesis of 3,4-dihydroquinoxalin-2-amine derivatives by a three-component coupling of one-pot condensation reactions in an aqueous medium
Kolla, Srinivasa Rao
Lee, Yong Rok
TETRAHEDRON, 2010, 66 (46) : 8938 - 8944
[25] ONE-POT, THREE-COMPONENT SYNTHESIS OF α-AMINOPHOSPHONATES CATALYZED BY ACYCLIC ACIDIC IONIC LIQUIDS
Fang, Dong
Jiao, Changmei
Ji, Baohua
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (12) : 2520 - 2526
[26] Silver-Catalyzed One-Pot Three-Component Selective Synthesis of β-Hydroxy Selenides
Leng, Tao
Wu, Ge
Zhou, Yun-Bing
Gao, Wenxia
Ding, Jinchang
Huang, Xiaobo
Liu, Miaochang
Wu, Huayue
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (22) : 4336 - 4340
[27] 2-Phenallyl as a versatile protecting group for the asymmetric one-pot three-component synthesis of propargylamines
Gommermann, N
Knochel, P
CHEMICAL COMMUNICATIONS, 2005, (33) : 4175 - 4177
[28] One-pot Three-component Condensation Reactions in Water. An Efficient and Improved Procedure for the Synthesis of Furan Annulated Heterocycles
Ahmad Shaabani
Mohammad Bagher Teimouri
Hamid Reza Bijanzadeh
Monatshefte für Chemie / Chemical Monthly, 2004, 135 : 589 - 593
[29] One-pot three-component condensation reactions in water. An efficient and improved procedure for the synthesis of furan annulated heterocycles
Shaabani, A
Teimouri, MB
Bijanzadeh, HR
MONATSHEFTE FUR CHEMIE, 2004, 135 (05): : 589 - 593
[30] Iodine-catalyzed one-pot three-component synthesis of homoallyl benzyl ethers from aldehydes
Kataki, Dolly
Phukan, Prodeep
TETRAHEDRON LETTERS, 2009, 50 (17) : 1958 - 1960

← 1 2 3 4 5 →