Synthesis of Hydroxypyrrolone Carboxamides Employing Selectfluor

被引：15

作者：

Allmann, Tim Carlo ^{[1
]}

Moldovan, Rares-Petru ^{[1
]}

Jones, Peter G. ^{[2
]}

Lindel, Thomas ^{[1
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, Hagenring 30, D-38106 Braunschweig, Germany

[2] Tech Univ Carolo Wilhelmina Braunschweig, Inst Inorgan & Analyt Chem, Braunschweig, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 01期

关键词：

heterocycles; marine natural products; oxidation; pyrroles; Selectfluor; MARINE SPONGE; SINGLET OXYGEN; NATURAL-PRODUCTS; BIOLOGICAL EVALUATION; A-C; ALKALOIDS; ISOCHRYSOHERMIDIN; PHYCOCYANOBILIN; INHIBITION;

D O I：

10.1002/chem.201503695

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reaction of pyrrole-2-carboxamides with Selectfluor in MeCN/water (4:1) affords 2-hydroxy-5-oxopyrrole-2-carboxamides in yields of up to 80%. A variety of sensitive functional groups is tolerated, among them aldehydes and alkynes. The new method also works in the presence of allyl groups and appears to be superior to the use of singlet oxygen. Reaction of the monobrominated dihydropyrrolo[1,2-a]pyrazinone mukanadin C and its nonbrominated analogue afforded bicyclic hydroxypyrrolones. These compounds are interesting as they constitute a partial structure of the marine natural product oxocyclostylidol.

引用

收藏

页码：111 / 115

页数：5

相关论文

共 34 条

[1] SYNTHESIS BY BENZILIC ACID REARRANGEMENT OF THE 2-OXO-3-PYRROLINE DIMERIC ALKALOID OF MERCURIALIS-LEIOCARPA [J].

ABE, K ;

OKADA, T ;

MASUI, Y ;

MIWA, T .

PHYTOCHEMISTRY, 1989, 28 (03) :960-960

[2]

[Anonymous], ANGEW CHEM

[3] First syntheses of the pyrroloketopiperazine marine natural products (±)-longamide, (±)-longamide B, (±)-longamide B methyl ester and (±)-hanishin [J].

Banwell, MG ;

Bray, AM ;

Willis, AC ;

Wong, DJ .

NEW JOURNAL OF CHEMISTRY, 1999, 23 (07) :687-690

[4] SYNTHETIC STUDIES RELEVANT TO BIOSYNTHETIC RESEARCH ON VITAMIN-B12 .7. SYNTHESIS OF (+/-)-BONELLIN DIMETHYL ESTER [J].

BATTERSBY, AR ;

DUTTON, CJ ;

FOOKES, CJR .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1569-1576

[5] Diversity-Oriented Approach to Pyrrole-Imidazole Alkaloid Frameworks [J].

Bhandari, Manojkumar R. ;

Yousufuddin, Muhammed ;

Lovely, Carl J. .

ORGANIC LETTERS, 2011, 13 (06) :1382-1385

[6] SINGLET OXYGEN MEDIATED OXIDATIVE DECARBOXYLATION OF PYRROLE-2-CARBOXYLIC ACIDS [J].

BOGER, DL ;

BALDINO, CM .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6942-6944

[7] LONGAMIDE AND 3,7-DIMETHYLISOGUANINE, 2 NOVEL ALKALOIDS FROM THE MARINE SPONGE AGELAS-LONGISSIMA [J].

CAFIERI, F ;

FATTORUSSO, E ;

MANGONI, A ;

TAGLIALATELASCAFATI, O .

TETRAHEDRON LETTERS, 1995, 36 (43) :7893-7896

[8] Armeniaspiroles, a new class of antibacterials: antibacterial activities and total synthesis of 5-chloro-Armeniaspirole A [J].

Couturier, Cedric ;

Bauer, Armin ;

Rey, Astrid ;

Schroif-Dufour, Cosima ;

Broenstrup, Mark .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (19) :6292-6296

[9] Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes [J].

Cui, Peng ;

Macdonald, Timothy L. ;

Chen, Meng ;

Nadler, Jerry L. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (13) :3401-3405

[10] Isolation and Structural Elucidation of Armeniaspirols A-C: Potent Antibiotics against Gram-Positive Pathogens [J].

Dufour, Cosima ;

Wink, Joachim ;

Kurz, Michael ;

Kogler, Herbert ;

Olivan, Helene ;

Sable, Serge ;

Heyse, Winfried ;

Gerlitz, Martin ;

Toti, Luigi ;

Nusser, Antje ;

Rey, Astrid ;

Couturier, Cedric ;

Bauer, Armin ;

Broenstrup, Mark .

CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (50) :16123-16128

← 1 2 3 4 →