An efficient and selective route to hybrid trifluoromethyl-substituted γ-lactones or fused nitrogen derivatives via cascade reactions

被引：2

作者：

Tucaliuc, Roxana ^{[4
]}

Cotea, Valeriu V. ^{[4
]}

Moldoveanu, Costel ^{[1
]}

Zbancioc, Gheorghita ^{[1
]}

Deleanu, Calin ^{[2
]}

Jones, Peter G. ^{[3
]}

Mangalagiu, Ionel I. ^{[1
]}

机构：

[1] Alexandru Ioan Cuza Univ, Dept Organ Chem, Iasi 700506, Romania

[2] P Poni Inst Macromol Chem, RO-700487 Iasi, Romania

[3] Tech Univ Carolo Wilhelmina Braunschweig, Inst Anorgan & Analyt Chem, D-38023 Braunschweig, Germany

[4] Univ Agr & Vet Med Ion Ionescu de la Brad, Iasi, Romania

来源：

TETRAHEDRON LETTERS | 2011年 / 52卷 / 48期

关键词：

Trifluoromethyl groups; gamma-Lactone; Fused nitrogen heterocycles; Cascade reaction; Diazine; IN-VITRO; DESIGN; POTENT; INHIBITORS; CHEMISTRY; ANALOGS; HIV;

D O I：

10.1016/j.tetlet.2011.09.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward, efficient and selective route for obtaining hybrid trifluoromethyl-substituted gamma-lactones and fused nitrogen heterocycles is presented. The reaction could be guided either to gamma-lactones with a nitrogen-containing heterocyclic skeleton (for monocyclic systems) or to fused nitrogen heterocycles (for fused bicyclic systems). A new class of gamma-lactone with a nitrogen heterocyclic skeleton was obtained. Feasible reaction mechanisms involving cascade reactions are presented. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：6439 / 6442

页数：4

共 21 条

[1] New pyridazine derivatives: Synthesis, chemistry and biological activity
Butnariu, Roxana M.
Mangalagiu, Ionel I.
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (07) : 2823 - 2829
[2] The design of drugs for HIV and HCV
De Clercq, Erik
[J]. NATURE REVIEWS DRUG DISCOVERY, 2007, 6 (12) : 1001 - 1018
[3] Some pyrrole substituted aryl pyridazinone and phthalazinone derivatives and their antihypertensive activities
Demirayak, S
Karaburun, AC
Beis, R
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (12) : 1089 - 1095
[4] Crystal structure and mechanism of a bacterial fluorinating enzyme
Dong, CJ
Huang, FL
Deng, H
Schaffrath, C
Spencer, JB
O'Hagan, D
Naismith, JH
[J]. NATURE, 2004, 427 (6974) : 561 - 565
[5] Synthesis and evaluation of novel chloropyridazine derivatives as potent human rhinovirus (HRV) capsid-binding inhibitors
Fan, Shi-Yong
Zheng, Zhi-Bing
Mi, Chun-Lai
Zhou, Xin-Bo
Yan, Hui
Gong, Ze-Hui
Li, Song
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (02) : 621 - 624
[6] Houk K.N., 1984, THEORY 13 DIPOLAR CY, V2, P407
[7] Klamann D., 1991, ORGANISCHE STICK B 1, VE14b, P1
[8] Synthesis and evaluation of 2-substituted-6-phenyl-4,5-dihydropyridazin-3(2H)-ones as potent inodilators
Kumar, Dinesh
Carron, Rosalia
De la Calle, Carmen
Jindal, Dharam Paul
Bansal, Ranju
[J]. ACTA PHARMACEUTICA, 2008, 58 (04) : 393 - 405
[9] Fluorinated methylenecyclopropane analogues of nucleosides.: Synthesis and antiviral activity of (Z)- and (E)-9-{[(2-fluoromethyl-2-hydroxymethyl)-cyclopropylidene]methyl}adenine and -guanine
Li, Chengwei
Prichard, Mark N.
Korba, Brent E.
Drach, John C.
Zemlicka, Jiri
[J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (05) : 2148 - 2155
[10] Synthesis and anti-HIV activity of 2′-fluorine modified nucleoside phosphonates:: Analogs of GS-9148
Mackman, Richard L.
Lin, Kuel-Ying
Bojamra, Constantine G.
Hui, Hon
Douglas, Janet
Grant, Deborah
Petrakovsky, Oleg
Prasad, Vidya
Ray, Adrian S.
Cihlar, Tomas
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (03) : 1116 - 1119

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