A new method for the synthesis of 1,3-oxathiolan-2-ones by the reaction of epoxides with sulfur and carbon monoxide

Nishiyama, Yutaka; Katahira, Chisato; Sonoda, Noboru

doi:10.1016/j.tetlet.2004.09.105

Cited by 23 publications

(12 citation statements)

References 7 publications

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“…[7] In contrast, the three-component reaction of sulfur, carbon monoxide, and an epoxide yielding oxathiolan-2-ones, though synthetically very useful, can yield only a rather limited number of products. [8] Different strategies for the design of molecular complexity using MCR chemistry have been devised. [9] We report herein a novel stereoselective Ugi-type reaction of the four highly variable starting materials: a-amino acid, oxo component, isocyanide, and primary or secondary amine, thus comprising a novel 4-CR.…”

Section: Dedicated To Ivar Ugimentioning

confidence: 99%

Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

et al. 2012

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Section: Dedicated To Ivar Ugimentioning

confidence: 99%

Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

et al. 2012

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“…Results were shown that the catalyst have a good specific surface area and high pore volume, this might be a reason for high catalytic performance of catalyst. FT-IR spectrum of Fe(HSO 4 ) 3 The FT-IR spectrum of the catalyst was shown in figure 3. The catalyst is solid and solid state IR spectrum was recorded using the KBr disk technique.…”

Section: Figurementioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] Amido-or amino ketone derivatives are important for their biological, pharmaceutical properties, 9,10 and in the preparation of antibiotic drugs such as nikomycine or neopolyoxines. 11,12 The common procedure for the synthesis of these class compounds is the Dakin-West reaction [13][14][15] which involves the condensation of α-amino acids with acetic anhydride in the presence of suitable base, [3][4][5][6][7][8][9][10][11][12][13][14][15][16] these reaction produce α-acetamido ketones ZnO, 29 Amberlyst-15, 30 iodine 31 and FeCl 3 .6H 2 O. 32 Ferric salts have applied for the formation of carbon-nitrogen and carbon-oxygen bonds in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

One-pot preparation of β–amido ketones and esters in four-component condensation reaction using ferric hydrogensulfate as effective and reusable catalyst

Shaterian¹,

Yarahmadi²,

Ghashang³

2008

Arkivoc

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A new one-pot and efficient four-component condensation of benzaldehyde derivatives, enolizable ketones, acetyl chloride and acetonitrile or benzonitrile in the presence of ferric hydrogensulfate as an inexpensive and effective catalyst for the synthesis of β-amido ketones and esters is described. The present methodology offers several advantages, such as good yields, short reaction times and a recyclable catalyst with a very easy work up.

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“…[7] On the other hand, the three component reaction of sulfur, carbon monoxide and epoxides yielding oxathiolan-2-ones, although synthetically very useful can yield only a rather limited number of products. [8] Different strategies for the design of molecular complexity using MCR chemistry have been devised. [9] We would like to report here on a novel stereoselective Ugitype reaction of the four highly variable starting materials α-amino acid, oxo-component, isocyanide and primary or secondary amine, thus comprising a novel true 4-CR.…”

Section: Introductionmentioning

confidence: 99%

Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

et al. 2012

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A truly 4-component reaction! In analogy to a galaxy consisting of millions of stars a multicomponent reaction scaffold can result in millions of compound variations. The MCR of α-amino acids, oxocomponents, isocyanides and primary or secondary amines is such a high-number high-diversity reaction providing an enormous potential for drug discovery or catalyst screening.Keywords multicomponent reaction; iminodicarboxamide scaffold; 4 component reaction; Ugi; isocyanide To Ivar Ugi, the father of modern multicomponent reaction chemistry Multicomponent reaction technology (MCR) is now widely recognized for its impact on drug discovery projects and is strongly endorsed by industry in addition to academia. [1] Thus an increasing number of products based on MCRs are marketed or in development. Recent examples include boceprevir, [2] retosiban [3] or mandipropamide, [4] just to name a few. While the number of described MCRs is enormous, only a small number has a wide breath in all classes of educts and allows for the quasi infinite variation of all starting materials. [5] The size of the chemical space of the different MCR scaffolds, however, has major implications on the usefulness of the particular MCR. For example, the classical Ugi four component reactions allows for the simultaneous variation of four very common starting materials (amine, oxo-component, carboxylic acid and isocyanide, which is derived from a primary amine). [6] Thus the number of synthesizable products is very large. [7] On the other hand, the three component reaction of sulfur, carbon monoxide and epoxides yielding oxathiolan-2-ones, although synthetically very useful can yield only a rather limited number of products. [8] Different strategies for the design of molecular complexity using MCR chemistry have been devised. [9] We would like to report here on a novel stereoselective Ugitype reaction of the four highly variable starting materials α-amino acid, oxo-component, isocyanide and primary or secondary amine, thus comprising a novel true 4-CR. 15 Years ago Ugi et al. described the first time the discovery of a novel variant of his reaction in this journal (Scheme 1). [10] The reaction was termed U-5C-4CR (5-center-4-component) because of the use of bireactive α-amino acids, oxo-components, isocyanides and alcohol as a solvent and reactant. The reaction proved to be versatile and several reports document their usefulness. [11] Remarkably, this reaction also lead to the first orally available potent, selective and non peptide oxytocin antagonist, currently undergoing clinical trials for preterm birth. [3,12] This reaction, however only comprises a MCR where three components show a great variability: the α-amino acid 1, the oxo-component 2 and the isocyanide 3. The variability of the alcohol component 4, which is also the solvent, is rather restricted towards low molecular weight liquids, e.g. MeOH and EtOH. The restriction is a result of the poor solubility of the amino acids in higher alcohols and their reduced nucleophilic reactivity...

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A new method for the synthesis of 1,3-oxathiolan-2-ones by the reaction of epoxides with sulfur and carbon monoxide

Cited by 23 publications

References 7 publications

Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

One-pot preparation of β–amido ketones and esters in four-component condensation reaction using ferric hydrogensulfate as effective and reusable catalyst

Efficient Assembly of Iminodicarboxamides by a “Truly” Four‐Component Reaction

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