Solution-Phase Parallel Synthesis of a Multisubstituted Cyclic Imidate Library

被引：18

作者：

Mehta, Saurabh ^{[1
,2
]}

Waldo, Jesse P. ^{[1
]}

Neuenswander, Benjamin ^{[3
,4
]}

Lushington, Gerald H. ^{[3
,4
]}

Larock, Richard C. ^{[1
]}

机构：

[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA

[2] Delhi Technol Univ, Dept Appl Chem, Delhi 110042, India

[3] Univ Kansas, NIH, Ctr Excellence Chem Methodol, Lawrence, KS 66047 USA

[4] Univ Kansas, Lib Dev, Lawrence, KS 66047 USA

来源：

ACS COMBINATORIAL SCIENCE | 2013年 / 15卷 / 05期

基金：

美国国家卫生研究院;

关键词：

solution-phase; parallel synthesis; iodocyclization; cyclic imidates; iminolactones; palladium coupling; DRUG-DELIVERY REVIEWS; ELECTROPHILIC CYCLIZATION; EFFICIENT SYNTHESIS; ESTIMATE SOLUBILITY; DIVERSE LIBRARY; ARYL; 2,3-ALLENAMIDES; IMINOLACTONES; CONSTRUCTION; PERMEABILITY;

D O I：

10.1021/co3001605

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The solution-phase parallel synthesis of a diverse 71-member library of multisubstituted cyclic imidates is described. The key intermediates, 3-iodomethylene-containing cyclic imidates, are readily prepared in good to excellent yields by the palladium/copper-catalyzed cross-coupling of various o-iodobenzamides and terminal alkynes, followed by electrophilic cyclization with I-2. These cyclic imidates were further functionalized by palladium-catalyzed Suzuki-Miyaura, Sonogashira, carbonylative amidation, and Heck chemistry using sublibraries of commercially available building blocks.

引用

页码：247 / 254

页数：8

共 34 条

[1] An improved method for the palladium-catalyzed amination of aryl iodides [J].

Ali, MH ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2560-2565

[2]

[Anonymous], 2008, SYBYL VERS 8 0

[3] Caco-2 monolayers in experimental and theoretical predictions of drug transport (Reprinted from Advanced Drug Delivery Reviews, vol 22, pg 67-84, 1996) [J].

Artursson, P ;

Palm, K ;

Luthman, K .

ADVANCED DRUG DELIVERY REVIEWS, 2001, 46 (1-3) :27-43

[4] Solution-Phase Synthesis of a Highly Substituted Furan Library [J].

Cho, Chul-Hee ;

Shi, Feng ;

Jung, Dai-Il ;

Neuenswander, Benjamin ;

Lushington, Gerald H. ;

Larockt, Richard C. .

ACS COMBINATORIAL SCIENCE, 2012, 14 (07) :403-414

[5] Parallel Synthesis of a Desketoraloxifene Analogue Library via lodocyclization/Palladium-Catalyzed Coupling [J].

Cho, Chul-Hee ;

Jung, Dai-Il ;

Neuenswander, Benjamin ;

Larock, Richard C. .

ACS COMBINATORIAL SCIENCE, 2011, 13 (05) :501-510

[6] Solution-Phase Parallel Synthesis of a Multi-substituted Benzo[b]thiophene Library [J].

Cho, Chul-Hee ;

Neuenswander, Benjamin ;

Lushington, Gerald H. ;

Larock, Richard C. .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2009, 11 (05) :900-906

[7]

Cruciani G., 2003, DRUG BIOAVAILABILITY, P406

[8] Three-component reactions involving zwitterionic intermediates for the construction of heterocyclic systems:: one pot synthesis of highly functionalized γ-iminolactones [J].

Esmaeili, AA ;

Zendegani, H .

TETRAHEDRON, 2005, 61 (16) :4031-4034

[9] Synthesis of Heterocycles via Electrophilic Cyclization of Alkynes Containing Heteroatom [J].

Godoi, Benhur ;

Schumacher, Ricardo F. ;

Zeni, Gilson .

CHEMICAL REVIEWS, 2011, 111 (04) :2937-2980

[10] PALLADIUM-CATALYZED VINYLIC HYDROGEN SUBSTITUTION REACTIONS WITH ARYL, BENZYL, AND STYRYL HALIDES [J].

HECK, RF ;

NOLLEY, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) :2320-&

← 1 2 3 4 →