New ferrocenyl-substituted heterocycles. Formation under Biginelli conditions, DFT modelling, and structure determination

被引：18

作者：

Kiss, K. ^{[1
]}

Csampai, A. ^{[1
]}

Sohar, P. ^{[1
,2
]}

机构：

[1] Eotvos Lorand Univ, Inst Chem, H-1117 Budapest, Hungary

[2] Eotvos Lorand Univ, Hungarian Acad Sci, Prot Modelling Grp, H-1117 Budapest, Hungary

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2010年 / 695卷 / 15-16期

基金：

匈牙利科学研究基金会;

关键词：

Ferrocene; Biginelli reaction; Diels-Alder addition; DFT calculations; NMR spectroscopy; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; CONDENSATION REACTION; IMPROVED PROTOCOL; DIHYDROPYRIMIDINONES; 3-COMPONENT; COMPLEXES; BENIGN;

D O I：

10.1016/j.jorganchem.2010.04.036

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of novel ferrocene-containing-dihydropyrimidines (DHPs) were prepared by three-component Biginelli reactions of formylferrocene, 1,3-dioxo-components and thiourea catalyzed by boric acid and ytterbium triflate, respectively. When cyclic-1,3-diones were employed as dioxo component in the reactions promoted by boric acid, besides one expected 4-ferrocenyl-2-thioxoquinazoline, 9-ferrocenyl-2H-xanthene-1,8-dione and 9-ferrocenylcyclopenta[b]chromen-8-ones could also be isolated as products. By means of control reactions and B3LYP/6-31 G(d) modelling the formation of the chromenone was interpreted by hetero-DielseAlder addition involving the Knoevenagel intermediate and the cyclopentadiene resulted in situ from acid-catalyzed decomposition of formylferrocene. The enhanced tendency of the acyclic dioxo components to undergo Biginelli reaction avoiding cycloaddition was reasoned by the formation of Knoevenagel intermediates capable of chelating proton or Lewis acids. The structures of the new compounds were established by IR and NMR spectroscopy, including HMQC, HMBC, DEPT and DNOE measurements. Some structural characteristics were disclosed by B3LYP/6-31 G (d) method. (C) 2010 Elsevier B. V. All rights reserved.

引用

页码：1852 / 1857

页数：6

共 31 条

[1]

[Anonymous], 1989, Density-functional theory of atoms and molecules

[2] In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α1A receptor antagonists for the treatment of benign prostatic hyperplasia [J].

Barrow, JC ;

Nantermet, PG ;

Selnick, HG ;

Glass, KL ;

Rittle, KE ;

Gilbert, KF ;

Steele, TG ;

Homnick, CF ;

Freidinger, RM ;

Ransom, RW ;

Kling, P ;

Reiss, D ;

Broten, TP ;

Schorn, TW ;

Chang, RSL ;

O'Malley, SS ;

Olah, TV ;

Ellis, JD ;

Barrish, A ;

Kassahun, K ;

Leppert, P ;

Nagarathnam, D ;

Forray, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) :2703-2718

[3] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[4] TRANSITION-METAL FULVENE COMPLEXES .14. CRYSTAL AND MOLECULAR-STRUCTURE OF FERROCENYLDIPHENYLCARBENIUM TETRAFLUOROBORATE - FULVENE-IRON COMPLEX [J].

BEHRENS, U .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 182 (01) :89-98

[5]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[6] STRUCTURE AND BONDING OF FERROCENYLCARBONIUM IONS [J].

DANNENBE.JJ ;

LEVENBER.MK ;

RICHARDS, JH .

TETRAHEDRON, 1973, 29 (11) :1575-1584

[7] Complexes of lanthanoids with neutral pi donor ligands [J].

Deacon, GB ;

Shen, Q .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1996, 506 (1-2) :1-17

[8] Model studies toward the synthesis of dihydropyrimidinyl and pyridyl α-amino acids via three-component biginelli and hantzsch cyclocondensations [J].

Dondoni, A ;

Massi, A ;

Minghini, E ;

Sabbatini, S ;

Bertolasi, V .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (16) :6172-6183

[9]

Frisch MJ, 2003, GAUSSIAN 03 REVISION

[10] Indium(III) halides-catalyzed preparation of ferrocene-dihydropyrimidinones [J].

Fu, NY ;

Yuan, YF ;

Pang, ML ;

Wang, JT ;

Peppe, C .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2003, 672 (1-2) :52-57

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