54022-34-3

Upstream product

• 22026-39-7 benzo[d][1,3]dioxole-5-carbohydrazide 
• 25054-53-9 3,4-(methylenedioxy)benzoyl chloride 
• 94-53-1 Piperonylic acid 
• 326-56-7 methyl 3,4-methylenedioxybenzoate 
• 2635-13-4 1,2-(methylenedioxy)-4-bromobenzene 

Downstream Products

• 69922-28-7 5-isocyanato-1,3-benzodioxole 
• 4421-09-4 piperonylonitrile 
• 119179-46-3 1-(benzo[d][1,3]dioxol-5-yl)urea 
• 471931-69-8 N-(phenylcarbamoyl)benzo[d][1,3]dioxole-5-carboxamide 
• 34060-22-5 N-methyl-3,4-(methylenedioxy)aniline 
• 950508-59-5 (αR,3aS,10bS)-5-carbethoxy-1-(1-phenyl-2-hydroxyethyl)-1,3a,4,10b-tetrahydro-3H,8H-[1,3]dioxolo[4,5-g]isoxazolo[4,3-c]quinoline 
• 950508-58-4 (αR,3aR,10bR)-5-carbethoxy-1-(1-phenyl-2-hydroxyethyl)-1,3a,4,10b-tetrahydro-3H,8H-[1,3]dioxolo[4,5-g]isoxazolo[4,3-c]quinoline 

Relevant academic research and scientific papers

Synthesis of: N -methylated amines from acyl azides using methanol

The transformation of acyl azide derivatives into N-methylamines was developed using methanol as the C1 source via the one-pot Curtius rearrangement and borrowing hydrogen methodology. Following this protocol, various functionalised N-methylated amines were synthesized using the (NNN)Ru(ii) complex from carboxylic acids via an acyl azide intermediate. Several kinetic studies and DFT calculations were carried out to support the mechanism and also to determine the role of the Ru(ii) complex and base in this transformation.

Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide

An efficient palladium-catalyzed chlorocarbonylation of aryl (pseudo)halides that gives access to a wide range of carboxylic acid derivatives has been developed. The use of butyryl chloride as a combined CO and Cl source eludes the need for toxic, gaseous carbon monoxide, thus facilitating the synthesis of high-value products from readily available aryl (pseudo)halides. The combination of palladium(0), Xantphos, and an amine base is essential to promote this broadly applicable catalytic reaction. Overall, this reaction provides access to a great variety of carbonyl-containing products through in situ transformation of the generated aroyl chloride. Combined experimental and computational studies support a reaction mechanism involving in situ generation of CO.

Direct conversion of carboxylic acids to various nitrogen-containing compounds in the one-pot exploiting curtius rearrangement

Herein we report, a single-pot multistep conversion of inactivated carboxylic acids to various N-containing compounds using a common synthetic methodology. The developed methodology rendered the use of carboxylic acids as a direct surrogate of primary amines, for the synthesis of primary ureas, secondary/tertiary ureas, O/S-carbamates, benzoyl ureas, amides, and N-formyls, exploiting the Curtius reaction. This approach has a potential to provide a diversified library of N-containing compounds, starting from a single carboxylic acid, based on the selection of the nucleophile.

Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles

An unprecedented protocol for the transformation of benzoyl azides into benzonitrile derivatives via iminophosphoranes generated in situ is described. The strategy was successfully applied to the de-novo synthesis of 2-alkenylated benzonitrile derivatives from benzoyl azides through ortho CH activation/alkenylation followed by subsequent rearrangement. The salient features of this protocol involve incorporation of two important functionalities through cyanation and olefination in one pot under mild reaction conditions by using a less expensive Ru catalyst. The mechanism was established by isolating and characterising (using 31PNMR) an intermediate with two ortho functionalities, iminophosphorane and olefin, under specific reaction conditions. Directly functional! Cyanation and olefination was accomplished in one pot from benzoyl azides through an unprecedented directing group transformation. The method generates benzonitriles and can be used for the synthesis of 2-alkenylated benzonitrile derivatives (see scheme).

Synthesis of enantiopure 4-amino-3-hydroxymethyl-tetrahydroquinolines via an intramolecular nitrone cycloaddition

Enantiopure 4-amino-3-hydroxymethyl-1,2,3,4-tetrahydroquinolines are synthesized by using an intramolecular cycloaddition of chiral nitrones prepared from aldehydes 5 and (R)-α-(hydroxymethyl)benzylhydroxylamine. Reaction times of the nitrone cycloadditio

Synthesis of N-methylphenanthridinone derivatives fused with a silacyclohexane ring by radical reaction using tributyltin hydride

Radical reaction of (N-methyl-7-bromo-2,2-dimethyl-2-silatetralin-6-ylamino)veratramide (8a) and -piperonamides (8b) in boiling benzene using tributyltin hydride and AIBN gave two kinds of N-methylphenanthridinone derivatives (15 and 16), which were cyclized at 6- and 2-positions of aroylic acid moiety. On the other hand, similar reaction of N-methyl-N-(2-bromoveratryl and 2-bromopiperonyl)-2,2-dimethyl-2-silatetralin-6-carboxamides (14) produced N-methylphenanthridinone deivatives (17) as each sole product, in which cyclization occurred at 5-position of 2-silatetralin moiety.

Bis(alkylthio)carbenes as novel reagents for organic synthesis

Bis(alkylthio)carbenes have been shown to be a useful class of reactive intermediates for applications to organic synthesis. Substituted hydroindolones, isatins and hydroquinolones can be prepared by the addition of these carbenes to vinyl isocyanates. (C) 2000 Elsevier Science Ltd.

Rapid construction of isatin derivatives via addition of bis(alkylthio)carbenes to aryl isocyanates

Thermally induced cyclization between bis(alkylthio)carbenes, derived from the corresponding oxadiazolines, and substituted aryl isocyanates provides access to a variety of isatin derivatives with good efficiency.

Synthesis and larvicidal activity of new substituted hydrazinylureas (substituted 1,4-diphenylsemicarbazides)

Substituted arylhydrazines 1a-j on condensation with 3,4-methylenedioxyphenyl isocyanate 2 in dry toluene afford new substituted hydrazinylureas 3a-j.Compounds, 3b, 3e, 3h, 3i have been found to be insecticidal against larvae of housefly (Musca domestica nebulo).