An expedient approach to synthesize fluorescent 3-substituted 4H-quinolizin-4-ones via (η4-vinylketene)-Fe(CO)3 complexes

被引:24
作者
Rosas-Sanchez, Alfredo [1 ]
Toscano, Ruben A. [2 ]
Lopez-Cortes, Jose G. [2 ]
Carmen Ortega-Alfaro, M. [1 ]
机构
[1] Univ Nacl Autonoma Mexico, Inst Ciencias Nucl, Mexico City 04510, DF, Mexico
[2] Univ Nacl Autonoma Mexico, Inst Quim, Mexico City 04510, DF, Mexico
基金
芬兰科学院;
关键词
RING-JUNCTION NITROGEN; TRICARBONYL(VINYLKETENE)IRON(0) COMPLEXES; DERIVATIVES; CONDENSATION; REACTIVITY; ALKYNES; DESIGN; VINYLKETENES; ACTIVATION; INHIBITORS;
D O I
10.1039/c4dt03021d
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An efficient and practical methodology for the synthesis of 3-substituted 4H-quinolizin-4-ones using (eta(4)-vinylketene)-Fe(CO)(3) complexes as key intermediates has been developed. The advantage of this transformation lies in the use of simple and readily available starting materials and mild carbonylation conditions. The fluorescent properties of these compounds were determined and the quantum yield was obtained, ranging from 0.04 to 0.36 depending on the substituent.
引用
收藏
页码:578 / 590
页数:13
相关论文
共 57 条
[1]   GENERATION OF HOMOCHIRAL QUATERNARY CARBON CENTERS FROM (VINYLKETENIMINE)TRICARBONYLIRON(0) COMPLEXES [J].
ALCOCK, NW ;
PIKE, GA ;
RICHARDS, CJ ;
THOMAS, SE .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :531-534
[2]   PREPARATION OF TRICARBONYL(ETA-4-VINYLKETENE)IRON(0) COMPLEXES FROM TRICARBONYL(ETA-4-VINYL KETONE)IRON(0) COMPLEXES AND THEIR SUBSEQUENT CONVERSION TO TRICARBONYL(ETA-4-VINYLKETENIMINE)IRON(0) COMPLEXES [J].
ALCOCK, NW ;
RICHARDS, CJ ;
THOMAS, SE .
ORGANOMETALLICS, 1991, 10 (01) :231-238
[3]  
Altomare G., 1994, J APPL CRYSTALLOGR, V27, P435, DOI DOI 10.1107/S002188989400021X
[4]  
Alvarez-Toledano C., 1997, J ORGANOMET CHEM, V549, P4
[5]   Condensed bridgehead nitrogen heterocyclic system: Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid [J].
Amir, Mohd ;
Kumar, Harish ;
Javed, S. A. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (10) :2056-2066
[6]   Enantioselective Michael addition of 2-nitropropane to chalcone analogues catalyzed by chiral azacrown ethers based on α-D-glucose and D-mannitol [J].
Bakó, T ;
Bakó, P ;
Keglevich, G ;
Báthori, N ;
Czugler, M ;
Tatai, J ;
Novák, T ;
Parlagh, G ;
Toke, L .
TETRAHEDRON-ASYMMETRY, 2003, 14 (13) :1917-1923
[7]  
Benoit L, 2004, [No title captured], Patent No. [2004014893, WO2004014893]
[8]   LiOH•H2O as a novel dual activation catalyst for highly efficient and easy synthesis of 1,3-diaryl-2-propenones by Claisen-Schmidt condensation under mild conditions [J].
Bhagat, S ;
Sharma, R ;
Sawant, DM ;
Sharma, L ;
Chakraborti, AK .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 244 (1-2) :20-24
[9]   SYNTHESIS OF ALPHA-PYRIDONE-BASED AZAHETEROAROMATICS BY INTRAMOLECULAR VINYLKETENE CYCLIZATIONS ONTO THE C=N BOND OF NITROGEN HETEROAROMATICS [J].
BIRCHLER, AG ;
LIU, FQ ;
LIEBESKIND, LS .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (25) :7737-7745
[10]   A STUDY OF SOME QUINOLIZONE DERIVATIVES [J].
BOEKELHEIDE, V ;
LODGE, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (08) :3681-3684