Note on the Electrolytic Methoxylation of Furan.

Clauson-Kaas, Niels; Tyle, Zdeněk; Dietrich, Paul; Stenhagen, Einar; Östling, Sven

doi:10.3891/acta.chem.scand.06-0962

Cited by 23 publications

(21 citation statements)

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“…The key starting intermediates 2 and 3 11 were prepared by reacting 2-nitroaniline or 2-fluoroaniline with 2,5-dimethoxytetrahydrofuran (DMTHF) in the presence of glacial acetic acid by a modified Paal-Knorr procedure 12-13 known as the Clauson-Kaas reaction 14 in 88% and 85%…”

Section: Methodsmentioning

confidence: 99%

Two alternatives for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives

Harrak¹,

Weber²,

Gomez³

et al. 2006

Arkivoc

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Dedicated to Professor Joan Bosch on the occasion of his 60th anniversary AbstractThe 4,5-dihydropyrrolo[1,2-a]quinoxaline system was prepared through two different reaction sequences. The first method is based on the intramolecular reductive amination of the corresponding nitrophenylpyrrole-carbaldehyde intermediate, whereas an alternative synthesis involves as key step, the intramolecular substitution of an aromatic fluoride by a secondary amine.

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Section: Methodsmentioning

confidence: 99%

Two alternatives for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives

Harrak¹,

Weber²,

Gomez³

et al. 2006

Arkivoc

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“…Treatment of 2 with 2,5-dimethoxytetrahydrofuran in acetic acid, according to the Clauson -Kaas method [14], afforded the pyrrolylthiophene carboxylate 3, which was converted into the corresponding carboxamide 4 in pyrrolidine at 708C. Cyclization of 4 in phosphorus oxychloride yielded an iminium chloride intermediate, which was treated with an aqueous solution of sodium hydroxide to yield the tricyclic ketone 5.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Anti‐tumor Activities of Novel Methylthio‐, Sulfinyl‐, and Sulfonyl‐8H‐thieno[2,3‐b]pyrrolizin‐8‐oximino Derivatives

Guo

Zhao

et al. 2007

Archiv der Pharmazie

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A series of novel methylthio-, sulfinyl-, and sulfonyl-8H-thieno[2,3-b]pyrrolizin-8-oximino derivatives 7A-12P was designed and synthesized as anti-tumor agents. Their structures were confirmed by IR, (1)H-NMR, MS, and elemental analysis. The anti-tumor activities of all the target compounds were tested by the MTT method in vitro against Bel-7402 (human liver cancer) and HT-1080 (human fibro sarcoma) cell lines. Among them, compound 11N (IC(50) = 18.2 microM, 8.2 microM), was the most promising compound of all synthesized molecules, it was 2.5- and 3.3-times more active than cisplatin (IC(50) = 45.2 microM, 26.7 microM), respectively.

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“…In a discussion of the use of tetrahydrofurans in the synthesis of heterocycles, first place must be given to the Clauson-Kaas synthesis of pyrroles from 2,5-dialkoxytetrahydrofurans LXXXII and primary amines [67][68][69]:…”

Section: Tetraiiydrofuransmentioning

confidence: 99%

Hydrofurans in the synthesis of heterocycles — A review

Vartanyan¹,

Елисеев²,

Skov³

et al. 1997

Chem Heterocycl Compd

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The use of hydrofurans in the synthesis of heterocyclic compounds is reviewed.Hydrofuran derivatives have been widely used as reagents. This results from theft great reactivity in combination with the possibility of obtaining them from cheap sources --furfural, furan, and tetrahydrofurfuryl alcohol [1]. Recently satisfactory methods have been developed based on hydrofurans for the synthesis of many 5-and 6-membered nitrogencontaining heterocycles, furans, thiophenes, tropinones, monosaccharides, and a number of condensed systems.The extensive material on the use of hydrofurans in heterocyclic synthesis has not yet been reviewed. We have decided to give a survey of methods and not a complete bibliography on the use of these compounds, which could not be contained within a single paper. For example the Clauson-Kass method for the synthesis of pyrroles alone has been cited as a routine procedure in tens of publications and patents. The literature on 2,5-dialkoxyhydrofurans is cited in a volume in which N. l~l'ming has presented an additional review of these compounds [2]. DIHYDROFURANSMost reactions of dihydrofurans which lead to the formation of other heterocycles can be divided into two large groups: a) various types of cycloaddition to the double bond with the formation of stable adducts which then undergo further conversions; b) nucleophilic scission of the C-O bond with recyclization (intramolecular recyclization is possible if a substituent on the furan ring contains a nucleophilic group in the chain). The unsubstituted adduct Ha (R = R 1 = R 2 = H) is used in the synthesis of isoindole [5] and porphyrins '[6]. The authors of the latter paper boiled compound Ha and its oxide (ILl) with benzyl carbamate in glacial acetic acid for many hours to give pyrroles which were converted further into the corresponding porphyrins (IV and V).

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Note on the Electrolytic Methoxylation of Furan.

Cited by 23 publications

References 0 publications

Two alternatives for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives

Two alternatives for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives

Synthesis and Anti‐tumor Activities of Novel Methylthio‐, Sulfinyl‐, and Sulfonyl‐8H‐thieno[2,3‐b]pyrrolizin‐8‐oximino Derivatives

Hydrofurans in the synthesis of heterocycles — A review

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