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
Abada, Zahra
Cojean, Sandrine
Pomel, Sebastien
Ferrie, Laurent
Akagah, Bernardin
Lormier, Anh Tuan
Loiseau, Philippe M.
Figadere, Bruno
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 67 : 158 - 165
[2] Identification of 2-oxo-N-(phenylmethyl)-4-imidazolidinecarboxamide antagonists of the P2X7 receptor
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.
[J]. 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
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.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (17) : 5080 - 5084
[4] PTEROIC ACID DERIVATIVES .6. UNEQUIVOCAL SYNTHESES OF SOME ISOMERIC GLUTAMIC ACID PEPTIDES
ANGIER, RB
WALLER, CW
HUTCHINGS, BL
BOOTHE, JH
MOWAT, JH
SEMB, J
SUBBAROW, Y
[J]. 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
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
[J]. 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
BACON, RGR
HILL, HAO
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1964, (MAR): : 1097 - +
[7] Synthesis and biological activity of novel MIF antagonists
Balachandran, Sarala
Gadekar, Pradip K.
Parkale, Santosh
Yadav, Vitthal N.
Kamath, Divya
Ramaswamy, Sneha
Sharma, Somesh
Vishwakarma, Ram A.
Dagia, Nilesh M.
[J]. 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
Bao, Weiliang
Liu, Yunyun
Lv, Xin
Oian, Weixing
[J]. ORGANIC LETTERS, 2008, 10 (17) : 3899 - 3902
[9] Synthesis of a new family of N-aryl lactams active on chemesthesis and taste
Bassoli, A
Borgonovo, G
Busnelli, G
Morini, G
[J]. 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
BELL, SC
CONKLIN, G
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (02) : 179 - &

← 1 2 3 4 5 6 7 8 9 10 →