Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

被引：11

作者：

Baudelet, Davy ^{[1
,2
,3
]}

Daich, Adam ^{[4
]}

Rigo, Benoit ^{[1
,2
]}

Lipka, Emmanuelle ^{[1
,3
]}

Gautret, Philippe ^{[1
,2
]}

Homerin, Germain ^{[1
,2
]}

Claverie, Christelle ^{[2
]}

Rousseau, Jolanta ^{[2
]}

Abuhaie, Cristina-Maria ^{[1
,2
,5
]}

Ghinet, Alina ^{[1
,2
,5
]}

机构：

[1] Univ Lille 2, Fac Med Pole Rech, CHRU Lille, Inserm,LIRIC U995, Pl Verdun, F-59045 Lille, France

[2] Ecole Hautes Etud Ingn HEI, Lab Pharmacochim, 13 Rue Toul, F-59046 Lille, France

[3] UFR Pharm Lille, Lab Chim Analyt, BP 83, F-59006 Lille, France

[4] Normandie Univ, CNRS, ULEHAVRE, URCOM, F-76600 Le Havre, France

[5] Alexandru Ioan Cuza Univ, Dept Organ Chem, Fac Chem, B Dul Carol I 11,Corp A, Iasi 700506, Romania

来源：

SYNTHESIS-STUTTGART | 2016年 / 48卷 / 14期

关键词：

arylation; heterogeneous catalysis; copper; cross-coupling; lactams; heterocycles; CATALYZED C-N; BETA-ENAMINO ESTERS; O BOND FORMATION; ARYL HALIDES; PRIVILEGED STRUCTURES; COUPLING REACTIONS; ELECTROCHEMICAL SYNTHESIS; NITROGEN NUCLEOPHILES; PYROGLUTAMIC ACID; AROMATIC-AMINES;

D O I：

10.1055/s-0035-1561415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp(2)-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.

引用

页码：2226 / 2244

页数：19

共 135 条

[1] Synthesis and antiprotozoal activity of original porphyrin precursors and derivatives [J].

Abada, Zahra ;

Cojean, Sandrine ;

Pomel, Sebastien ;

Ferrie, Laurent ;

Akagah, Bernardin ;

Lormier, Anh Tuan ;

Loiseau, Philippe M. ;

Figadere, Bruno .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 67 :158-165

[2] Identification of 2-oxo-N-(phenylmethyl)-4-imidazolidinecarboxamide antagonists of the P2X7 receptor [J].

Abberley, Lee ;

Bebius, Aude ;

Beswick, Paul J. ;

Billinton, Andy ;

Collis, Katharine L. ;

Dean, David K. ;

Fonfria, Elena ;

Gleave, Robert J. ;

Medhurst, Stephen J. ;

Michel, Anton D. ;

Moses, Andrew P. ;

Patel, Sadhana ;

Roman, Shilina A. ;

Scoccitti, Tiziana ;

Smith, Beverley ;

Steadman, Jon G. A. ;

Walter, Daryl S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (22) :6370-6374

[3] Discovery and structure-activity relationships of a series of pyroglutamic acid amide antagonists of the P2X7 receptor [J].

Abdi, Muna H. ;

Beswick, Paul J. ;

Billinton, Andy ;

Chambers, Laura J. ;

Charlton, Andrew ;

Collins, Sue D. ;

Collis, Katharine L. ;

Dean, David K. ;

Fonfria, Elena ;

Gleave, Robert J. ;

Lejeune, Clarisse L. ;

Livermore, David G. ;

Medhurst, Stephen J. ;

Michel, Anton D. ;

Moses, Andrew P. ;

Page, Lee ;

Patel, Sadhana ;

Roman, Shilina A. ;

Senger, Stefan ;

Slingsby, Brian ;

Steadman, Jon G. A. ;

Stevens, Alexander J. ;

Walter, Daryl S. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) :5080-5084

[4] PTEROIC ACID DERIVATIVES .6. UNEQUIVOCAL SYNTHESES OF SOME ISOMERIC GLUTAMIC ACID PEPTIDES [J].

ANGIER, RB ;

WALLER, CW ;

HUTCHINGS, BL ;

BOOTHE, JH ;

MOWAT, JH ;

SEMB, J ;

SUBBAROW, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (01) :74-77

[5] Potent inhibition of influenza sialidase by a benzoic acid containing a 2-pyrrolidinone substituent [J].

Atigadda, VR ;

Brouillette, WJ ;

Duarte, F ;

Ali, SM ;

Babu, YS ;

Bantia, S ;

Chand, P ;

Chu, N ;

Montgomery, JA ;

Walsh, DA ;

Sudbeck, EA ;

Finley, J ;

Luo, M ;

Air, GM ;

Laver, GW .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (13) :2332-2343

[6] METAL IONS + COMPLEXES IN ORGANIC REACTIONS .I. SUBSTITUTION REACTIONS BETWEEN ARYL HALIDES + CUPROUS SALTS IN ORGANIC SOLVENTS [J].

BACON, RGR ;

HILL, HAO .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (MAR) :1097-+

[7] Synthesis and biological activity of novel MIF antagonists [J].

Balachandran, Sarala ;

Gadekar, Pradip K. ;

Parkale, Santosh ;

Yadav, Vitthal N. ;

Kamath, Divya ;

Ramaswamy, Sneha ;

Sharma, Somesh ;

Vishwakarma, Ram A. ;

Dagia, Nilesh M. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (05) :1508-1511

[8] Cu2O-catalyzed tandem ring-opening/coupling cyclization process for the synthesis of 2,3-dihydro-1,4-benzodioxins [J].

Bao, Weiliang ;

Liu, Yunyun ;

Lv, Xin ;

Oian, Weixing .

ORGANIC LETTERS, 2008, 10 (17) :3899-3902

[9] Synthesis of a new family of N-aryl lactams active on chemesthesis and taste [J].

Bassoli, A ;

Borgonovo, G ;

Busnelli, G ;

Morini, G .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (07) :1656-1663

[10] RING CLOSURE REACTIONS WITH NITRILES .I. FORMATION OF PYRROLO[2,1-C][1,2,4]BENZOTHIADIAZINES AND PYRROLO[1,2-A]QUINAZOLINES [J].

BELL, SC ;

CONKLIN, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (02) :179-&

← 1 2 3 4 5 6 7 8 9 10 →