Methylene Blue as a Photosensitizer and Redox Agent: Synthesis of 5-Hydroxy-1H-pyrrol-2(5H)-ones from Furans

被引：71

作者：

Kalaitzakis, Dimitris ^{[1
]}

Kouridaki, Antonia ^{[1
]}

Noutsias, Dimitris ^{[1
]}

Montagnon, Tamsyn ^{[1
]}

Vassilikogiannakis, Georgios ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Iraklion 71003, Crete, Greece

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 21期

基金：

欧洲研究理事会;

关键词：

furan oxidation; methylene blue; singlet oxygen; sustainable chemistry; -unsaturated; -lactams; ONE-POT SYNTHESIS; OXIDATION; 5-HYDROXY-3-PYRROLIN-2-ONES; DERIVATIVES; EFFICIENT; LACTAMS; DIMETHYLDIOXIRANE; TRANSFORMATION; PSEUDOESTERS; CYCLIZATION;

D O I：

10.1002/anie.201500744

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessible furans into 5-hydroxy-1H-pyrrol-2(5H)-ones has been developed. The methodology was extended to the synthesis of other high-value ,-unsaturated -lactams. This useful set of transformations relies not only on the photosensitizing ability of methylene blue, but also on its redox properties: properties that have until now been virtually ignored in a synthetic context.

引用

页码：6283 / 6287

页数：5

共 60 条

[1]

Adamcíková L, 1999, INT J CHEM KINET, V31, P463, DOI 10.1002/(SICI)1097-4601(1999)31:6<463::AID-KIN8>3.0.CO

[2]

2-2

[3] Synthesis of N-substituted γ-methylene γ-lactams [J].

Adhikari, R ;

Jones, DA ;

Liepa, AJ ;

Nearn, RH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 2005, 58 (12) :882-890

[4] Visible-Light Organic Photocatalysis for Latent Radical-Initiated Polymerization via 2e-/1H+ Transfers: Initiation with Parallels to Photosynthesis [J].

Aguirre-Soto, Alan ;

Lim, Chern-Hooi ;

Hwang, Albert T. ;

Musgrave, Charles B. ;

Stansbury, Jeffrey W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (20) :7418-7427

[5] Stereoselective synthesis of the pyrroloisoquinoline ring system [J].

Allin, SM ;

James, SL ;

Martin, WP ;

Smith, TAD ;

Elsegood, MRJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :3029-3036

[6] THE TETRACYCLIC ERYTHRINA ALKALOIDS [J].

AMER, ME ;

SHAMMA, M ;

FREYER, AJ .

JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :329-363

[7] What Is Happening When the Blue Bottle Bleaches: An Investigation of the Methylene Blue-Catalyzed Air Oxidation of Glucose [J].

Anderson, Laurens ;

Wittkopp, Stacy M. ;

Painter, Christopher J. ;

Liegel, Jessica J. ;

Schreiner, Rodney ;

Bell, Jerry A. ;

Shakhashiri, Bassam Z. .

JOURNAL OF CHEMICAL EDUCATION, 2012, 89 (11) :1425-1431

[8]

[Anonymous], 2012, Angew. Chem.

[9]

Azmat R., 2009, REDUCTION METHYLENE, P1

[10] Synthesis of new 3-(1-ethylsulfanyl-2-perfluoroalkyl)-5-hydroxy-5-methyl (or 5-phenyl)-1,5-dihydro-pyrrol-2-ones starting from γ-keto thioesters and amines [J].

Bouillon, JP ;

Tinant, B ;

Nuzillard, JM ;

Portella, C .

SYNTHESIS-STUTTGART, 2004, (05) :711-721

← 1 2 3 4 5 6 →