Phosphine(III)-Triggered One-Pot Domino Sequences towards 5,6-Dihydropyridine-2-(1H)-One and Pyridine-2(1H)-One Scaffolds

被引：1

作者：

Makra, Zsofia ^{[1
]}

Madacsi, Ramona ^{[1
]}

Martinek, Tamas A. ^{[2
]}

Benyei, Attila ^{[3
]}

Puskas, Laszlo G. ^{[1
]}

Gyuris, Mario ^{[1
]}

Kanizsai, Ivan ^{[1
]}

机构：

[1] AVIDIN Ltd, Also Kikoto Sor 11-D, H-6726 Szeged, Hungary

[2] Univ Szeged, Dept Med Chem, Dom Ter 8, H-6720 Szeged, Hungary

[3] Univ Debrecen, Dept Phys Chem, Lab Xray Diffract, Egyet Ter 1, H-4032 Debrecen, Hungary

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 06期

关键词：

Phosphine(III); One-pot domino synthesis; Mannich precursor; 5; 6-Dihydropyridine-2(1H)-one; Pyridine-2(1H)-one; BAYLIS-HILLMAN REACTION; VINYLOGOUS ALDOL REACTION; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; CATALYZED REACTION; ACRYLAMIDE; PHOSPHINE; DERIVATIVES; DIHYDROPYRIDINONE; ENHANCEMENT;

D O I：

10.1002/adsc.202101370

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An elegant P(nBu)(3)-triggered synthetic approach has been developed towards multisubstituted 5,6-dihydropyridin-2(1H)-one and pyridin-2(1H)-one derivatives exploiting a domino process involving retro-Claisen/intra-MBH/Wittig/vinylogous aldol transformations as well as retro-Claisen/intra-MBH/ylide hydrolysis/oxidation sequences. This transformation demonstrates chemo- and regioselectivity as well as accessible high diversity enchancement in 17-90% isolated yield.

引用

页码：1134 / 1143

页数：10

共 74 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
Ackermann, Lutz
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
[2] Catalytic crossed Michael cycloisomerization of thioenoates:: Total synthesis of (±)-ricciocarpin A
Agapiou, K
Krische, MJ
[J]. ORGANIC LETTERS, 2003, 5 (10) : 1737 - 1740
[3] Correlation between pKa and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction:: Discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope
Aggarwal, VK
Emme, I
Fulford, SY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) : 692 - 700
[4] [2+2+2] Cyclotrimerization of Alkynes and Isocyanates/Isothiocyanates Catalyzed by Ruthenium-Alkylidene Complexes
Alvarez, Silvia
Medina, Sandra
Dominguez, Gema
Perez-Castells, Javier
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19) : 9995 - 10001
[5] [Anonymous], 2005, Angew. Chem, V117, P4760
[6] The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction
Basavaiah, D
Rao, PD
Hyma, RS
[J]. TETRAHEDRON, 1996, 52 (24) : 8001 - 8062
[7] The Baylis-Hillman reaction: a new continent in organic chemistry - our philosophy, vision and over three decades of research
Basavaiah, Deevi
Naganaboina, Ram Tilak
[J]. NEW JOURNAL OF CHEMISTRY, 2018, 42 (17) : 14036 - 14066
[8] Acryl Activation by Intramolecular Hydrogen Bond: Morita Baylis Hillman Reaction of Acrylamide with Broad Substrate Scope
Bharadwaj, Kishor Chandra
[J]. CHEMISTRYSELECT, 2017, 2 (19): : 5384 - 5389
[9] Intramolecular Morita-Baylis-Hillman and Rauhut-Currier reactions. A catalytic and atom economic route for carbocycles and heterocycles
Bharadwaj, Kishor Chandra
[J]. RSC ADVANCES, 2015, 5 (93): : 75923 - 75946
[10] Base catalyzed synthesis of bicyclo[3.2.1]octane scaffolds
Boehringer, Regis
Geoffroy, Philippe
Miesch, Michel
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (25) : 6940 - 6943

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