Reformatsky reactions with N-arylpyrrolidine-2-thiones: synthesis of tricyclic analogues of quinolone antibacterial agents

Michael, Joseph P.; Koning, Charles B. de; Hosken, Gladys D.; Stanbury, Trevor V.

doi:10.1016/s0040-4020(01)00964-4

Cited by 98 publications

(52 citation statements)

References 37 publications

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“…However, the most important chemotherapeutic agents to contain an embedded enaminone component are without doubt the quinolone antibacterials. In particular, the fluorinated quinolones are amongst the most effective broadspectrum oral antibacterial agents developed to date [76].One-pot transformations of pyrrolidine enaminones 93 into 5-(3-aminopropyl)isoxazoles and the corresponding pyrazoles were achieved with hydroxylamine in an a c e t a t e -b u ffered solution and with hydrazine sulfate, respectively ( Figure 37). The ring transformation sequence allowed simple access to heterocycles which are histamine analogues and both enaminones and heterocycles possess histaminergic activity [77,78].…”

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Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Negri

Kascheres

2004

Journal of Heterocyclic Chem

179

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Enaminoketones and esters are gaining increased interest, particularly cyclic-β-enaminoesters, which are known as important intermediates for the synthesis of heterocycles and natural products, because the enantioselective preparation of highly functionalized compounds is of central importance in synthetic chemistry. Enaminones are versatile synthetic intermediates that combine the ambident nucleophilicity of enamines with the ambident eletrophilicity of enones. Enaminoketones and enaminonitriles have proven to be versatile building blocks for the synthesis of various heterocycles such as pyridine, pyrimidine and pyrrole derivatives. Enaminones systems have "enone" character, and may act as acceptors in both 1,2 and 1,4-additions. In this way the enaminone serves as a scaffold for annulation, and can gain access to systems such as pyrroles indolizidines, quinolizidines and perhydroindoles, all of which are common motifs in alkaloid structures. Enaminones are frequently employed as building blocks for the preparation of a variety of bicyclic compounds of biological interest and have been recently recognized as potential anticonvulsant compounds. Since a large number of developments in the use of enaminones in heterocyclic synthesis have occurred, a review of the recent developments in the synthetic approaches, covering the literature since 1995 until 2004, to these interesting molecules and their useful chemical transformations and biological activity can be considered of considerable value.J. Heterocyclic Chem., 41, 461 (2004).Enaminoketones. Introduction.The term enaminone was introduced by Greenhill to define the enamine of a 1,3-diketone, β-ketoester or similar 1,3-difunctional reagents, and is used to indicate any compound containing the conjugated system N-C=C-C=O [1]. Enaminones are versatile synthetic intermediates that combine the ambident nucleophilicity of enamines with the ambident eletrophilicity of enones. The chemistry of the enaminocarbonyl group 1 is potentially an area of considerable scope when one considers that there are present in this moiety, three nucleophilic sites (a, c and e) and two electrophilic sites (b and d) [2][3][4] (Figure 1).Theorically, primary and secondary acyclic enaminones can exist in three tautomeric forms: ketamino form, iminoenol form and oxoimino form [1][2][3]. There is also evidence that cyclic enaminones exist primarily in the enaminoketo form. A study of cyclic enaminoketones shows that these compounds have a significant steric fator in the six-membered ring. The six-membered ring enaminoketones are only slightly stronger bases than the saturated amines, whereas five-and-seven membered rings are much stronger bases than saturated amines. This has been attributed to a large steric strain present in six-membered enaminoketones [5].β-Aminoenones or enaminoketones can exist in four conformations owing to restricted rotations around the C=C double and C-C=O single bonds [3]. Enaminones with primary or secondary amino groups can exist in both Z-and E-forms. If there is a...

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“…(Figure 36), and a synthetic analogue of the duocarmycin class of antitumour agents [75,76]. However, the most important chemotherapeutic agents to contain an embedded enaminone component are without doubt the quinolone antibacterials.…”

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confidence: 99%

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Negri

Kascheres

2004

Journal of Heterocyclic Chem

179

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“…5,6 The ferrocene derivatives exhibit also an antiplasmodial, [7][8][9] antitumor, 10 and DNA cleaving 12 activities, have an antiproliferative effects on the MCF7 cell lines, 11 activity and have chemotherapeutic action on drugresistant cancer. 4,13 On the other hand, enaminones are important building blocks in the synthesis of many heterocyclic compounds 14 and many therapeutic: antitumor, 15 antimicrobial, [15][16][17] anticonvulsant, 18 antiinflammatory, 19 analgesic, 19 ulcerogenic agents. 20 Keeping in view the biological importance of enaminones, 18,21 we have recently reported 22 the synthesis of (Z)-3-adamantyl-1-aryl-prop/but-2-en-1-ones which were tested for anti-inflammatory and anticancer properties.…”

Section: Introductionmentioning

confidence: 99%

Ultrasound assisted synthesis of 1-amino-3-ferrocenyl-3-oxoprop-1-enes

Vishwakarma¹,

Khanikar²,

Kalita³

et al. 2018

10.5267/j.ccl

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“…β-Enaminones and β-enaminoesters are valuable intermediates for the synthesis of different bioactive molecules [1] including antibacterial, antitumor, and anticonvulsant agents [2]. They are also used for the preparation of amino acids [3], aminols [4,5], peptides [6], and alkaloids [7].…”

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confidence: 99%

An efficient chemo‐ and stereoselective synthesis of enaminones and enaminoesters using (bromodimethyl)sulfonium bromide under solvent‐free conditions

Das

Kanth

Majhi

et al. 2008

Heteroatom Chemistry

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Reformatsky reactions with N-arylpyrrolidine-2-thiones: synthesis of tricyclic analogues of quinolone antibacterial agents

Cited by 98 publications

References 37 publications

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Recent development in preparation reactivity and biological activity of enaminoketones and enaminothiones and their utilization to prepare heterocyclic compounds

Ultrasound assisted synthesis of 1-amino-3-ferrocenyl-3-oxoprop-1-enes

An efficient chemo‐ and stereoselective synthesis of enaminones and enaminoesters using (bromodimethyl)sulfonium bromide under solvent‐free conditions

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