Chemistry of Butenolides

Rao, Yong

doi:10.1021/cr60230a002

Cited by 192 publications

(66 citation statements)

References 135 publications

(196 reference statements)

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“…[10][11][12][13][14][15][16][17][18][19][20][21][22][23] For instance, the tetrahydrothiophene structural motif is present in various natural products and pharmacologically active molecules (Figure 1, top). [10][11][12] 2(3H)-Furanones, commonly known as Δ β,γ -butenolides, are another group of biologically relevant molecules that has been successfully applied in the target-oriented organic synthesis (Figure 1, middle).…”

Section: Introductionmentioning

confidence: 99%

“…[10][11][12] 2(3H)-Furanones, commonly known as Δ β,γ -butenolides, are another group of biologically relevant molecules that has been successfully applied in the target-oriented organic synthesis (Figure 1, middle). [13][14][15][16][17][18] Furthermore, this group of unsaturated γ-lactones is also widely distributed in nature. Owing to their interesting biological properties, α,α-disubstituted amino acids occupy a prominent position among biologically relevant compounds (Figure 1, bottom).…”

Section: Introductionmentioning

confidence: 99%

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Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif

Hejmanowska¹,

Albrecht²

2016

Arkivoc

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In this manuscript a new organocatalytic approach to spirocyclic tetrahydrothiophenes bearing either a butenolide or an azlactone moiety is described. The developed methodology is based on the cascade reactivity of 2-mercaptoacetaldehyde (generated in situ from 1,4-dithiane-2,5-diol) with α,β-unsaturated butenolides or azlactones, that consists of a thio-Michael addition followed by an intramolecular aldol reaction. Chiral bases derived from cinchona alkaloids are used as a catalyst promoting the cascade and controlling its stereochemical outcome.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif

Hejmanowska¹,

Albrecht²

2016

Arkivoc

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“…2-Oxo-2,5-dihydrofuran subunit has been found both in several bioactive natural (ascorbic, penicillic and tetronic acids), synthetic products [1][2][3][4][5][6][7][8][9][10][11] and in a number of drugs with diverse biological activities, such as antifungal, antibacterial and anti-inflammatory.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Bis-Iminodihydrofurans

Tokmajyan¹,

Karapetyan²

2015

Journal of the Brazilian Chemical Society

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A new synthetic pathway to new bis-iminodihydrofurans is proposed, which involves the synthesis of N-substituted iminodihydrofurans from reaction of iminodihydrofurans with 2-cyanoacetohydrazide and their condensation with tertiary a-hydroxyketones. This sequence of reactions opens the new approach to the synthesis of novel polyheteroconjugated systems consisting from iminodihydrofuran rings. The methodology is simple, rapid and inexpensive affording high yields of the potentially bioactive products.

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“…In recent years, there has been a great interest in preparing butenolides [1][2][3][4][5][6][7][8] containing compounds due to the biological effects attributed to this class of natural products such as freelingyne, rubrolides, etrenolin-furanosesquiterpenoid, Protoanemonin [9][10][11]. Among these bioactive compounds, there exist the alkylidenes butenolides, which have a large spectrum of biological activity [12][13][14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some Butenolides and Study of their Antibacterial Activity

Tamma

Gherraf

2013

ILCPA

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Butenolides and their analogues represent a wide range of natural compounds of a medical and biological importance. In the last decades, a great number of compounds of various structures, in general from Alkylidene butenolide, were isolated and showed biological activities. In this work we have studied the reactivity of some alkylidene butenolide and their antibacterial activity. the study is of a scientific interest in terms of the synthesis of new compounds (Butenolide 01: 5-hydroxy-5-(1-methoxypropan-2-yl)-4-methylfuran-2(5H)-one, Butenolide 02:5-(1-methoxypropan-2-yl)-4-methylfuran-2(5H)-one) that have not been studied before by other researchers; and of an economic importance because of its synthesis process which is easy and inexpensive. Moreover, butenolide showed a positive antimicrobial activity (antibiotic) against pathogenic bacteria (mainly Enterobacter hafniae).

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Chemistry of Butenolides

Cited by 192 publications

References 135 publications

Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif

Organocatalytic asymmetric approach to spirocyclic tetrahydrothiophenes containing either a butenolide or an azlactone structural motif

Synthesis of New Bis-Iminodihydrofurans

Synthesis of some Butenolides and Study of their Antibacterial Activity

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