95395-72-5

Upstream product

• 101938-15-2 benzyl-(4,5,6,7-tetrahydro-benz[c]isoxazol-3-yl)-amine 
• 100-46-9 benzylamine 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 100-52-7 benzaldehyde 
• 100869-90-7 benzylidene-(4,5,6,7-tetrahydro-benz[c]isoxazol-3-yl)-amine 
• 13054-47-2 4,5,6,7-tetrahydro-benzo[c]isoxazol-3-ylamine 
• 28637-56-1 2,2-dimethyl-5,6,7,8-tetrahydro-4H-benzo[d][1,3]dioxin-4-one 

Relevant academic research and scientific papers

An efficient and rapid synthesis of β-carboxamide derivatives using 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones by microwave irradiation

A general, efficient and rapid method for the synthesis of various β-carboxamide derivatives using microwave irradiation is described. Excellent isolated yields were obtained in very short reaction times when conventional heating was replaced by microwave irradiation.

Eco-friendly access to β-ketoamides: One-step catalyst-and solvent-free amidation of β-ketoesters under microwave irradiation

A highly efficient and facile catalyst- and solvent-free one step amidation of β-ketoesters, without using any additional reagents, is described. Therefore, β-ketoamides are obtained in good to excellent yields by condensation of β-ketoesters with various primary or secondary amines. This eco-friendly protocol has been developed under microwave irradiation.

Highly Diastereo- and Enantioselective Synthesis of α-Spiro-δ-lactams by an Organocascade Reaction

An asymmetric synthesis of α-spiro-δ-lactams by an organocascade reaction of easily accessible starting materials has been accomplished. The catalytic sequence begins with enantioselective Michael addition of a β-ketoamide to an α,β-unsaturated aldehyde,

Aminolysis of 2,2-difluoro-4-alkoxy-1,3,2-dioxaborinanes: route to β-keto amides and β-enamino carboxamides

4-Alkoxy substituted 1,3,2-dioxaborinanes 1, readily available from β-keto esters, undergo substitution reactions under mild reaction conditions with primary and secondary amines, deriving the 4-alkylamino analogue 2. Reactions of 1 with substituted phenylhydrazines gave the corresponding hydrazones, or pyrazolones, and 5-alkoxy-1H-pyrazoles as a mixture of products.

A new regio- and chemoselective approach to β-keto amides and β-enamino carboxamides via 1,3,2-dioxaborinanes

Surprisingly, 5,6-disubstituted 2,2-difluoro-4-alkoxy-1,3,2-dioxaborinanes, which can be easily obtained from β-keto esters, reacted regio- and chemoselectively with amines under mild reaction conditions to form 2,2-difluoro-4-alkylamino-1,3,2-dioxaborina

Asymmetric formation of quaternary centers through aza-annulation of chiral β-enamino amides with acrylate derivatives

The stereoselective formation of six-membered nitrogen heterocycles that contain an asymmetric quaternary carbon center was achieved through aza- annulation of β-enamino amide substrates with activated acrylate derivatives. Condensation of a racemic β-keto amide with an optically active primary amine, either (R)-α-methylbenzylamine or α-amino esters, generated the corresponding optically active tetrasubstituted secondary enamine, in which the enamine tautomer was stabilized through conjugation with an amide carbonyl. Treatment of the intermediate enamine with acryloyl chloride, acrylic anhydride, or sodium acrylate/ethyl chloroformate resulted in aza- annulation to give the corresponding δ-lactam with high diastereoselectivity (>96% de). For the variety of different β-enamino amide substrate classes examined in this reaction, the optimum method for activation of the acrylate derivative was the use of EtO2CCl. When aza-annulation was performed with an α-acetamido-substituted acrylate derivative, the stereoselective formation of the quaternary carbon center was accompanied by poor selectivity for generation of the center α to the lactam carbonyl. Crystallographic analysis of one α-amido aza-annulation product was performed to identify the key structural features of these molecules.

Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H,4H-1,3-dioxin-4-ones

Thermal reaction of 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones (1) with amines was studied.Acylketenes 2, generated by heating of 1, reacted with anilines and benzylamine to give the corresponding β-ketocarboxamides (3,4, and 5) in good yields.The reaction of 1 with ammonia gave 3-amino-2-alkenamides (7), which were hydrolyzed to β-ketocarboxamides (6).The former products 7 were readily transformed to the 6-substituted 2-methyl-3H-pyrimidin-4-ones (9) via the 3-acetamido-2-alkenamides (8).Acylation of O-benzylhydroxylamine with 1 gave the β-ketohydroxamic acids 10.Debenzylation of 10 followed by cyclization gave rise to 5-alkyl-3-hydroxyisoxazoles (12).The reaction of 1 with amides gave the corresponding N-acetylated amides (13). Keywords --- 2H,4H-1,3-dioxin-4-one; thermal fragmentation; acylketene; acylation; carboxamide; hydroxamic acid; 3-hydroxyisoxazole; 3H-pyrimidin-4-one