Aza-Conjugate Addition Methodology for the Synthesis of N-Hydroxy-isoindolin-1-ones

被引：23

作者：

Royo, Santiago ^{[2
]}

Chapman, Robert S. L. ^{[1
]}

Sim, Alisia M. ^{[1
]}

Peacock, Lucy R. ^{[1
]}

Bull, Steven D. ^{[1
]}

机构：

[1] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England

[2] Univ Jaume 1, Dept Quim Inorgan & Organ, Castellon de La Plana, Spain

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 05期

基金：

英国工程与自然科学研究理事会;

关键词：

GAMMA-BUTYROLACTONE; EFFICIENT SYNTHESIS; HYDROXAMIC ACIDS; ANALOGS; DERIVATIVES; ANTAGONIST; ISOINDOLINONES; ENANTIOMERS; INHIBITORS; REDUCTION;

D O I：

10.1021/acs.orglett.6b00261

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aryl-aldehydes containing ortho-substituted propiolate fragments react with hydroxylamine to afford carbinolamine intermediates that undergo intramolecular aza-conjugate addition reactions to afford N-hydroxy-2.3-dihydro-isoindolin-l-ones that can be reduced to their corresponding isoindolin-l-ones and isoindoles.

引用

页码：1146 / 1149

页数：4

共 32 条

[1] Asymmetric Synthesis of Fluorinated Isoindolinones through Palladium-Catalyzed Carbonylative Amination of Enantioenriched Benzylic Carbamates [J].

Barrio, Pablo ;

Ibanez, Ignacio ;

Herrera, Lidia ;

Roman, Raquel ;

Catalan, Silvia ;

Fustero, Santos .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (32) :11579-11584

[2] Isoindolinone enantiomers having affinity for the dopamine D4 receptor [J].

Belliotti, TR ;

Brink, WA ;

Kesten, SR ;

Rubin, JR ;

Wustrow, DJ ;

Zoski, KT ;

Whetzel, SZ ;

Corbin, AE ;

Pugsley, TA ;

Heffner, TG ;

Wise, LD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) :1499-1502

[3] Entonalactams A-C: Isoindolinone derivatives from an Australian rainforest fungus belonging to the genus Entonaema [J].

Choomuenwai, Vanida ;

Beattie, Karren D. ;

Healy, Peter C. ;

Andrews, Katherine T. ;

Fechner, Nigel ;

Davis, Rohan A. .

PHYTOCHEMISTRY, 2015, 117 :10-16

[4] Total synthesis of exochelin MN and analogues [J].

Dong, L ;

Miller, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14) :4759-4770

[5] STEREOSELECTIVE DOUBLE ALKYLATION OF ETHYL N-BOC-PYROGLUTAMATE [J].

EZQUERRA, J ;

PEDREGAL, C ;

RUBIO, A ;

VAQUERO, JJ ;

MATIA, MP ;

MARTIN, J ;

DIAZ, A ;

NAVIO, JLG ;

DEETER, JB .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4327-4331

[6] Synthesis and antimalarial evaluation of prodrugs of novel fosmidomycin analogues [J].

Faisca Phillips, Ana Maria ;

Nogueira, Fatima ;

Murtinheira, Fernanda ;

Barros, Maria Teresa .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (10) :2112-2116

[7] Nitroalkylation and nitroalkenylation reactions of γ-lactone enolates.: A facile ring switch from polysubstituted γ-lactones to polysubstituted γ-lactams [J].

Forzato, C ;

Nitti, P ;

Pitacco, G ;

Valentin, E ;

Morganti, S ;

Rizzato, E ;

Spinelli, D ;

Dell'Erba, C ;

Petrillo, G ;

Tavani, C .

TETRAHEDRON, 2004, 60 (48) :11011-11027

[8] Ruthenium-catalyzed reduction of N-alkoxy- and N-hydroxyamides [J].

Fukuzawa, Hiroko ;

Ura, Yasuyuki ;

Kataoka, Yasutaka .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (23) :3643-3648

[9] Ring expansions of acyloxy nitroso compounds [J].

Hadimani, Mallinath B. ;

Mukherjee, Rajeswari ;

Banerjee, Ranjan ;

Shoman, Mai E. ;

Aly, Omar M. ;

King, S. Bruce .

TETRAHEDRON LETTERS, 2015, 56 (43) :5870-5873

[10] Synthesis of isoindoles and related iso-condensed heteroaromatic pyrroles [J].

Heugebaert, Thomas S. A. ;

Roman, Bart I. ;

Stevens, Christian V. .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (17) :5626-5640

← 1 2 3 4 →