Preparation and reactions of thieno[3,2-b]furan derivatives

1986 ◽  
Vol 51 (8) ◽  
pp. 1685-1691 ◽  
Author(s):  
Eva Kraľovičová ◽  
Alžbeta Krutošíková ◽  
Jaroslav Kováč
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Acid Chloride ◽  
Thionyl Chloride ◽  
Acid Chlorides ◽  
Carboxylic Acid Chloride ◽  
Furan Derivatives ◽  
Nucleophilic Reactions ◽  
Triethylbenzylammonium Chloride

Reactions of 3-(5-aryl-2-furyl)propenoic, 3-(2-benzo[b]furyl)propenoic and 3-(5-ethoxycarbonyl-4H-furo[3,2-b]-2-pyrrolyl)propenoic acids with thionyl chloride in the presence of triethylbenzylammonium chloride were investigated. The obtained 2-arylthieno[3,2-b]-furan-5-carboxylic acid chlorides Ia - Ic and 3-chlorothieno[3,2-b]benzo[b]furan-2-carboxylic acid chloride afforded in substitution nucleophilic reactions the corresponding esters V and carboxylic acids VI which were decarboxylated to VII. 3-Chlorothieno[3,2-b]benzo[b]furan-2-carboxylic acid chloride (Id), 6-ethoxycarbonyl-3-chlorothieno[2',3':4,5]furo[3,2-b]pyrrole-2-carboxylic acid chloride (IV), and ethyl 3-chlorothieno[2',3':4,5]furo[3,2-b]indole-2-carboxylate (VIII), synthesized under conditions of triethylphosphite reduction from ethyl 6-chloro-2-(2-nitrophenyl)thieno[3,2-b]furan-5-carboxylate (Va), are new heterocyclic systems.

Über die Umsetzung von Benzylmalonylchlorid mit verschiedenen Natriumsalzen von Carbonsäuren / The Reaction of Benzylmalonyl Chloride with Sodium Salts of Carboxylic Acids

1972 ◽  
Vol 27 (5) ◽  
pp. 528-530 ◽  
Author(s):  
Helga Wittmann ◽  
Helmut Rathmayr
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Acid Chloride ◽  
Sodium Benzoate ◽  
Sodium Acetate ◽  
The Other ◽  
Carboxylic Acid Chloride ◽  
Sodium Salts ◽  
Other Hand ◽  
Sodium Phenylacetate

Benzylmalonyl Chloride reacts in the presence of sodium acetate in boiling benzene to give tribenzyl-phloroglucinol-triacetate, however with sodium chloroacetate to 3,5-dibenzyl-6-phenethylpyran-2,4-dion. In both cases trimerisation of benzylketene or benzylketene carboxylic acid chloride occurs. On the other hand, benzylmalonylchloride reacts with sodium benzoate and sodium phenylacetate via a dimeric benzylketene carboxylic acid chloride under the loss of phosgene to yield cyclopentadienyl derivatives.

scholarly journals Synthesis and Characterization of the Germathioacid Chloride Coordinated by an N-Heterocyclic Carbene §

Inorganics ◽  
2018 ◽  
Vol 6 (3) ◽  
pp. 76 ◽  
Author(s):  
Yasunobu Egawa ◽  
Chihiro Fukumoto ◽  
Koichiro Mikami ◽  
Nobuhiro Takeda ◽  
Masafumi Unno
Keyword(s):  
Carboxylic Acid ◽  
Density Functional ◽  
Dft Calculation ◽  
Acid Chlorides ◽  
Carboxylic Acid Chloride ◽  
Functional Theory ◽  
Nitrogen Ligands ◽  
Bond Property ◽  
Nitrogen Bonds

Carboxylic acid chlorides are useful substrates in organic chemistry. Many germanium analogues of carboxylic acid chloride have been synthesized so far. Nevertheless, all of the reported germathioacid chlorides use bidentate nitrogen ligands and contain germanium-nitrogen bonds. Our group synthesized germathioacid chloride, Ge(S)Cl{C6H3-2,6-Tip2}(Im-i-Pr2Me2), using N-heterocyclic carbene (Im-i-Pr2Me2). As a result of density functional theory (DFT) calculation, it was found that electrons are localized on sulfur, and the germanium-sulfur bond is a single bond with a slight double bond property.

Synthesis of amino acid diazoketones

1986 ◽  
Vol 64 (11) ◽  
pp. 2097-2102 ◽  
Author(s):  
George R. Pettit ◽  
Paul S. Nelson
Keyword(s):  
Amino Acid ◽  
Carboxylic Acid ◽  
Acid Chloride ◽  
Low Temperatures ◽  
Oxalyl Chloride ◽  
Acyl Chloride ◽  
Carboxyl Group ◽  
Carboxylic Acid Chloride ◽  
Active Esters ◽  
Active Ester

A study of carboxylic acid → diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids. The Arndt–Eistert route employing carboxylic acid chloride intermediates was found best (52% yield, 5b), performed at very low temperatures employing oxalyl chloride in dimethylformamide–tetrahydrofuran followed by diazomethane at −23 °C. Alternatively, substitution of a mixed carbonic anhydride for the acyl chloride led to very similar yields (57% of 5b) of diazoketones (5). Among a series of active ester intermediates (7) examined, only the ODnp (7d) and SPfp (7f) esters were found to react (23–26% yield), at least partially, with diazomethane. The latter two reactions appear to represent the first such examples employing active esters.

ChemInform Abstract: A New Synthesis of β,γ-Alkenyl Carboxylic Acids from α,β-Alkenyl Carboxylic Acid Chlorides and α,β-Alkenyl Aldehydes with One-Carbon Elongation.

ChemInform ◽  
2010 ◽  
Vol 33 (12) ◽  
pp. no-no
Author(s):  
Tsuyoshi Satoh ◽  
Akira Nakamura ◽  
Atsuko Iriuchijima ◽  
Yasumasa Hayashi ◽  
Ko-ichi Kubota
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Acid Chlorides ◽  
New Synthesis

scholarly journals Formamide catalyzed activation of carboxylic acids – versatile and cost-efficient amidation and esterification

2019 ◽  
Vol 10 (31) ◽  
pp. 7399-7406 ◽  
Author(s):  
Peter H. Huy ◽  
Christelle Mbouhom
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Bond Formation ◽  
Acid Chlorides ◽  
Cost Efficient

Formamide catalysis enables highly cost-efficient amide C–N and ester C–O bond formation through carboxylic acid chlorides as essential intermediates.

Synthesis and Reactions of Some 1H-Pyrazole-3 Carboxylic Acid Chloride

2009 ◽  
Vol 15 (4) ◽  
Author(s):  
İhan Özer İlhan ◽  
Sevgi Zühal ◽  
Zülbiye Önal ◽  
Emin Saripinar
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Carboxylic Acid Chloride

scholarly journals Synthesis and Screening of Substituted Thiadiazoles Against Gleophyllum Straitum

2004 ◽  
Vol 1 (3) ◽  
pp. 184-188
Author(s):  
M. G. H. Zaidi ◽  
Seema Zaidi ◽  
I. P. Pandey
Keyword(s):  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
Wood Preservation ◽  
Acid Chlorides

Cyclocondensation of a series of substituted phenoxy methylene carboxylic acids with thiosemoicarbazides afforded 2-Amino-5-Aryloxy Methylene –1,3,4 Thiadiazoles (Ia-Ie). The later were subsequently condensed with different phenoxymethylene carboxylic acid chlorides into 2- Aryloxy Methyleneamido-5-Aryloxy Methylene–1,3,4-Thiadiazoloyl Amides. The wood preservation efficiency of the both class of compounds was evaluated against a wood rotting fungusGleophyllum Straitumat different concentrations using food poison technique. In general phenoxy derivatives have shown more control over the growth ofGleophyllum Straitumthan their corresponding aminothiadiazoles at 500 ppm. The chlorophenoxy-substituted thiadiazoles among all have shown more activity then others againstGleophyllum Straitum.

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