Synthesis, structure, and fluorescence of isomeric indolizinediones. Carbonyl-bridged isodipyrrinones

被引：6

作者：

Boiadjiev, SE ^{[1
]}

Lightner, DA ^{[1
]}

机构：

[1] Univ Nevada, Dept Chem, Reno, NV 89557 USA

来源：

MONATSHEFTE FUR CHEMIE | 2005年 / 136卷 / 04期

关键词：

pyrrole; indolizinedione; fluorescence quantum yield;

D O I：

10.1007/s00706-004-0247-x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In "one-pot" reactions, pyrrole-alpha- and beta-aldehydes condense readily with 4-ethyl-3-methyl-3-pyrrolin-2-one to give isodipyrrinone analogs, which undergo intramolecular cyclization when the pyrrolealdehyde possesses an alpha or beta-CO2R group. The resulting regioisomeric pyrroloindolizinediones, with structures confirmed by NMR analysis, exhibit strong fluorescence, with quantum yields (phi(F)) as high as 0.91 at lambda(em) similar to 450-550 nm.

引用

收藏

页码：553 / 565

页数：13

相关论文

共 22 条

[1]

[Anonymous], 1890, BER DTSCH CHEM GES, DOI DOI 10.1002/CBER.189002301243

[2] PREPARATION OF SOME PYRROLE-3,4-DICARBOXYLIC ACID-DERIVATIVES AND THE CRYSTAL-STRUCTURE OF 2-METHYLPYRROLO[3,4-C]PYRROLE-1,3(2H,5H)-DIONE [J].

ARNOLD, DP ;

NITSCHINSK, LJ ;

KENNARD, CHL ;

SMITH, G .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1991, 44 (02) :323-330

[3] Intensely fluorescent dipyrrinones [J].

Boiadjiev, SE ;

Lightner, DA .

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2004, 17 (08) :675-679

[4]

BOIADJIEV SE, 2004, IN PRESS J ORG CHEM

[5] Synthesis and spectroscopic properties of a new class of strongly fluorescent dipyrrinones [J].

Brower, JO ;

Lightner, DA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (08) :2713-2716

[6] PYRROLES + RELATED COMPOUNDS .4. MASS SPECTROMETRY IN STRUCTURAL + STEREOCHEMICAL PROBLEMS .30. MASS SPECTRA OF MONOCYCLIC DERIVATIVES OF PYRROLE [J].

BUDZIKIEWICZ, H ;

NEWMAN, DJ ;

JACKSON, AH ;

WILSON, JM ;

DJERASSI, C ;

KENNER, GW .

JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :1949-&

[7] Synthesis of a 10-oxo-bilirubin: Effects of the oxo group on conformation, transhepatic transport, and glucuronidation [J].

Chen, QQ ;

Huggins, MT ;

Lightner, DA ;

Norona, W ;

McDonagh, AF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9253-9264

[8] CHEMISTRY OF PYRROLIC COMPOUNDS .16. BETA-ELECTRONEGATIVELY SUBSTITUTED DIPYRRYLMETHINES [J].

CLEZY, PS ;

LIEPA, AJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1971, 24 (09) :1933-&

[9] The formation of dipyrrolopyridones m the course of a proposed porphyrin synthesis [J].

Corwin, AH ;

Buc, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :1151-1156

[10]

DEZELIC M, 1960, GLASNIK DRUSTVA HEMI, V9, P49