Conversion of some azaheterocyclic-acetic esters and -acetonitriles into fused heterocycles

McKinnon, David M.; Spevack, P.A.; Tipples, Graham

doi:10.1139/v88-370

Cited by 10 publications

(3 citation statements)

References 5 publications

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“…The major product was cyanopyridobenzimidazole 145 formed by initial reaction of acetonitrile at the unsubstituted 5‐position of the dithiole ring, followed by ring opening and recyclization. The other product was dithiole 146 (Scheme ) [89].…”

Section: Synthesis Of Fused Benzimidazolesmentioning

confidence: 99%

1H‐Benzimidazole‐2‐acetonitriles as synthon in fused benzimidazole synthesis

Dawood

Elwan

Farahat

et al. 2010

Journal of Heterocyclic Chem

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Section: Synthesis Of Fused Benzimidazolesmentioning

confidence: 99%

1H‐Benzimidazole‐2‐acetonitriles as synthon in fused benzimidazole synthesis

Dawood

Elwan

Farahat

et al. 2010

Journal of Heterocyclic Chem

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“…And it had to be easily removed in high yield (a stipulation made more acute by the presence of six such groups per molecule). The triisopropylsilyl group failed us because subsequent demethylation of the sulfur by two different routes (t-BuSNa in dimethylformamide (DMF) and Na in NH 3 ) , gave low yields due to decomposition or byproducts. We ended up using the tert -butyl group despite the fact that its installation (eq 1) took place with only a moderate yield of 58% .…”

Section: Synthesismentioning

confidence: 99%

Synthesis and Properties of Water-Soluble Asterisk Molecules

Menger

Azov

2002

J. Am. Chem. Soc.

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An asterisk is comprised of six semirigid arms projecting from a benzene nucleus. In the case at hand, asterisks were synthesized with one, two, or three aromatic rings (connected by sulfur atoms) in each of the six arms. A phosphomonoester at the termini of each arm solubilized the asterisks in water. The colloidal properties of these amphiphilic molecules were investigated by UV−vis and fluorescence spectroscopy, calorimetry, light scattering, surface tensiometry, and pulse-gradient spin−echo NMR. Solubility, solubilization, metal binding, and micelle “seeding” experiments were also carried out. Chain-conformation and supramolecular assembly into remarkable molecular “scrolls” were investigated by X-ray analysis and electron microscopy, respectively. One of the more interesting properties of the asterisks is that they remain monomeric in water despite having as many as 19 hydrophobic aromatic rings exposed to the water. The reasons for this behavior, and the possibility of exploiting it for constructing enzyme models free from aggregation equilibria, are discussed.

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“…Eine Ujsung aus 620 mg (2 mmol) k in 60 ml Nitromethan wird bei (13) und (E,Z)-S-MethyIthio-2-/1 -(rnethylthio-thiocarbonyl)methyliden]-l,3dithio-4-carbothiosaure-S-methylester (14) Eine geriihne Suspension aus 564 mg (2 mmol) 3a in 70 ml CH2C1 wird mit 2 ml Hiinig-Base versetzt. Die Lasung v e M t sich sofort dunkelrot.…”

Section: (Z)-4-ethyl-5-methylthio-3-(i-nitromethyliden)-3h-12-dithiounclassified

Zur Reaktion von 3,5‐Bis(methylthio)‐1,2‐dithiolium‐Salzen mit CH‐aciden Verbindungen

Popp

Hartke

1994

Archiv der Pharmazie

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3,5-Bis(rnethylthio)-1,2-dithiolium -Salze a H b c 813 160 83 pTd 2Oc207 m c& 134 89Zur Reaktion von 3,5-Bis(methylthio)-1,2-dithiolium-Salzen mit CH-aciden Verbindungen Xue-ping PoppReaction of 3,S-Bis(methylthio)-L,2-dithiolium Salts with CH-Acidic Substrates Condensation of the 3,5-bis(methylthio)-1.2-dithiolium tetrafluoroborates 3a-q catalyzed by ethyl diisopropyl amine, with malonodinitrile leads to the thiophenes 9a-c. With methyl cyanoacetate the thiophenes 9d-f as well as the 3-alkylidene-l,2-dithioles 10a-e are formed. Nitromethane gives rise to the thiophenes 9g, 12 and to the 3-alkylidene-1.2-dithiole 1Od. By self condensation of 3a the trithiapentalene 13 and the isotrithiapentalene Die 3,5-Bis(methylthio)-1,2-dithiolium-tetrafluoroborate 3a-c kondensieren in Gegenwart von Ethyl-diisopropylamin mit Malondinitril zu den Thiophenen 9a-c, mit Cyanessigsauremethylester zu den Thiophenen 9d-f sowie zu den 3-Alkyliden-1.2-dithiolen l0a-c und mit Nitromethan zu den Thiophenen 9g, 12 sowie dem 3-Alkyliden-1,2-dithioIlOd. Die Selbstkondensation von 3a ergibt das Trithiapentalen 13 und das Isotrithiapentalen 14.14 are obtained.1.2-Dithiolium-Salze 1 sind leichl zuginglich und zeigen eine hohe Reaktivitit gegeniiber nucleophilen Reaklionspartnern'). Der Angriffson des Nucleophils hingt von seinen Eigenschaften sowie denen des 1.2-Dithiolium-Salzes ab. So kann das Nucleophil die S,S-Bindung spalten oder sich an C-3 bzw. C-5 addieren. Auch eine Deprotonierung des a-Kohlenstoffs im Substituenten R unter Bildung einer semicyclischen Doppelbindung oder ein g2nzlicher Verlust von R als Kation unter Erzeugung einer Carbenzwischenstufe wurden beobachtet. -R * R 0s-s s-s@ 11 12 13 14 E I 4Arch. Pharm. (Weinheim) 327,813-817 (1994) 3,5-Bis(methylthio)-1,2-dithiolium -Salze

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Conversion of some azaheterocyclic-acetic esters and -acetonitriles into fused heterocycles

Cited by 10 publications

References 5 publications

1H‐Benzimidazole‐2‐acetonitriles as synthon in fused benzimidazole synthesis

1H‐Benzimidazole‐2‐acetonitriles as synthon in fused benzimidazole synthesis

Synthesis and Properties of Water-Soluble Asterisk Molecules

Zur Reaktion von 3,5‐Bis(methylthio)‐1,2‐dithiolium‐Salzen mit CH‐aciden Verbindungen

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