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Ultrasound-assisted synthesis and biological evaluation of 1,4-benzodioxane-2-carboxyl-amino acids and Peptides

A series of peptides containing 1,4-benzodioxane nucleus were attempted to synthesize by conventional as well as green techniques like microwave-assisted and sonication, using dicyclohexylcarbodiimide (DCC) as a coupling reagent and triethylamine as a base. Sonication has proved to be the efficient method for the synthesis of the title compounds. All the compounds were characterized by FTIR, 1H NMR and Mass spectral studies. They were evaluated for their insecticidal and anthelmintic activities. All the compounds showed moderate anthelmintic activity as compared to the standard drug mebendazole. However, the compounds exhibited potent insecticidal activity, the most potent being 1,4-benzodioxane-2-carboxyl-phenylalaninetryptophan- methyl ester as compared to the standard, chloropyrifos.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Photocatalytic decarboxylative alkenylation of alpha-amino and alpha-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from alpha-amino and alpha-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Synthesis and biological activity of novel carbacyclins having bicyclic substituents on the omega-chain

A number of carbacyclins having bicyclic substituents on the omega-chain have been synthesized and tested for antiplatelet aggregation activity in vitro (against collagen-induced aggregation of rat platelet), for reduction of systemic blood pressure in vivo (ability to reduce the blood pressure in anesthetized rat by iv injection), and for cytoprotective activity (protection against ethanol-induced rat gastric lesion). The most effective compound for each activity was [3aS-[2E,3aalpha,4alpha(3R),5beta,6aalpha]]-5-[hexahydro-5-hydroxy-4-[3-hydroxy-3-(2- indanyl)-1-propynyl]-2(1H)-pentalenylidene]pentanoic acid (compound 11a), while some 1,4-benzodioxan analogues had selectivity for organ-protective activity, and indan analogues showed selectivity in their antiaggregation activity.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Oxidative decarboxylative radical trifluoromethylthiolation of alkyl carboxylic acids with silver(i) trifluoromethanethiolate and selectfluor

A straightforward silver-mediated oxidative decarboxylative radical trifluoromethylthiolation reaction of aliphatic carboxylic acid is described. This reaction operates under mild conditions and allows the synthesis of various valuable alkyltrifluoromethylthioethers from abundant alkyl carboxylic acids and convenient nucleophilic AgSCF3 reagent. It provides a practical and efficient approach for the preparation of alkyltrifluoromethylthioethers.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

Simple exploration of (S)-1,4-Benzodioxane-2-carboxylic acid

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Silver catalyzed decarboxylative direct C2-alkylation of benzothiazoles with carboxylic acids

A novel and efficient silver catalyzed decarboxylative direct C2-alkylation of benzothiazoles with carboxylic acids for the synthesis of 2-alkyl benzothiazoles was developed.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Decarboxylative Negishi Coupling of Redox-Active Aliphatic Esters by Cobalt Catalysis

A cobalt-catalyzed decarboxylative Negishi coupling reaction of redox-active aliphatic esters with organozinc reagents was developed. The method enabled efficient alkyl?aryl, alkyl?alkenyl, and alkyl?alkynyl coupling reactions under mild reaction conditions with no external ligand or additive needed. The success of an in situ activation protocol and the facile synthesis of the drug molecule (¡À)-preclamol highlight the synthetic potential of this method. Mechanistic studies indicated that a radical mechanism is involved.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Decarboxylative Acetoxylation of Aliphatic Carboxylic Acids

Organic molecules bearing acetoxy moieties are important functionalities in natural products, drugs, and agricultural chemicals. Synthesis of such molecules via transition metal-catalyzed C-O bond formation can be achieved in the presence of a carefully chosen directing group to alleviate the challenges associated with regioselectivity. An alternative approach is to use ubiquitous carboxylic acids as starting materials and perform a decarboxylative coupling. Herein, we report conditions for a photocatalytic decarboxylative C-O bond formation reaction that provides rapid and facile access to the corresponding acetoxylated products. Mechanistic investigations suggest that the reaction operates via oxidation of the carboxylate followed by rapid decarboxylation and oxidation by Cu(OAc)2

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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One-pot synthesis of thieno [2,3-d] pyrimidin-4-ol derivatives mediated by polyphosphonic anhydride

An efficient synthesis of thiopyrimidines with different substituents in position 2 is described. A rapid, mild and high yielding microwave-assisted one-pot cyclization of 5-substituted 2-amino thiophene-3-carboxamide derived from Gewald reaction1 with T3P and different acids gives the corresponding thiopyrimidines. The significant feature of this method includes less reaction time, high purity and reduced toxicity of the reaction.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

A new application about (S)-1,4-Benzodioxane-2-carboxylic acid

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Silver-Catalyzed Decarboxylative Radical Azidation of Aliphatic Carboxylic Acids in Aqueous Solution

We report herein an efficient and general method for the decarboxylative azidation of aliphatic carboxylic acids. Thus, with AgNO3 as the catalyst and K2S2O8 as the oxidant, the reactions of various aliphatic carboxylic acids with tosyl azide or pyridine-3-sulfonyl azide in aqueous CH3CN solution afforded the corresponding alkyl azides under mild conditions. A broad substrate scope and wide functional group compatibility were observed. A radical mechanism is proposed for this site-specific azidation.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Antihypertensive 4-amino-2-[4-(1,4-benzodioxan-2-carbonyl) piperazin-1-yl or homopiperazin-1-yl]quinazolines

Compounds having the formula STR1 and pharmaceutically acceptable salts thereof wherein R represents 6,7-di(lower alkoxy) or 6,7,8-tri(lower alkoxy); m is 1 or 2, X is –CHR1 — or –CH2 CH2 –; each R1 and R0 may be the same or different and is hydrogen or lower alkyl; each of R2 and R3 is hydrogen, lower alkoxy, lower alkyl, halogen, lower alkanoyl, lower alkoxycarbonyl, –CONR4 R5 or –SO2 NR4 R5 wherein each of R4 and R5 is hydrogen or lower alkyl; processes for their preparation; and their use as regulators of the cardiovascular system, and particularly in the treatment of hypertension.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem