82085-86-7

Upstream product

• 118-92-3 anthranilic acid 
• 5344-90-1 2-Aminobenzyl alcohol 
• 780-25-6 N-benzylidene benzylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 103200-12-0 1,2-dihydro-2-phenyl-1-p-tolylsulphonyl-3,1-benzoxazine 
• 1722-07-2 (2-(benzylamino)phenyl)methanol 
• 147611-22-1 2-(benzylamino)benzaldehyde 
• 1022-46-4 2-phenyl-4H-3,1-benzoxazin-4-one 
• 33768-43-3 N-(2-formylphenyl)benzamide 
• 46707-86-2 2-phenyl-4H-benzo[d][1,3]oxazine 
• 449-55-8 6,11-dihydro-5H-dibenzo[b,e]azepine 

Relevant academic research and scientific papers

Ring-chain tautomerism of the novel 2-ferrocenyl-2,4-dihydro-1H-3,1- benzoxazine

The synthesis and the study of the spectroscopic and electrochemical properties as well as the solution behavior of the novel 2-ferrocenyl-2,4- dihydro-1H-3,1-benzoxazine (1a) are described. NMR studies reveal the existence of a tautomeric equilibria between the cyclic (1a) and the open-chain form (2a). Electrochemical studies based on cyclic voltametry and 57Fe Moessbauer spectroscopy as well as a comparative study of the ring-chain tautomerism of 1a and that of 2-phenyl-2,4-dihydro-1H-3,1-benzoxazine (3a) are also reported.

Synthesis of (η6-arene)tricarbonylchromium derivatives of 1,4-dihydro-3,1-benzoxazines

A series of (η6-arene)tricarbonylchromium derivatives of 1,4-dihydro-3,1-benzoxazines was synthesized and characterized. The compounds were obtained by two alternative methods, namely, by the reaction of triammine(tricarbonyl)chromium with 1,4-dihydro-3,1-benzoxazines (method A) and by the condensation of (η6-2-aminobenzyl alcohol)tricarbonylchromium with various aldehydes and ketones (method B). The composition and structure of obtained compounds were established by different physicochemical methods of analysis, such as HPLC, UV, IR, 1H NMR spectroscopy, mass spectrometry, and X-ray diffraction.

Phosphine-Catalyzed Reaction between 2-Aminobenzaldehydes and Dialkyl Acetylenedicarboxylates: Synthesis of 1,2-Dihydroquinoline Derivatives and Toward the Development of an Olefination Reaction

A series of 1,2-dihydroquinolines were synthesized in good to excellent yields by reacting 2-aminobenzaldehyde derivatives and dialkyl acetylenedicarboxylates with catalytic amounts of phosphine. This reaction was rendered catalytic by the selective in situ phosphine oxide reduction with the use of phenylsilane. Furthermore, with the same starting materials and with an additional role of the reducing agent, a new olefination reaction was discovered. Hydrogen/deuterium (H/D) exchange experiments revealed the possible mechanism of this reaction.

Iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines: Synthesis of quinazolines by trapping of ammonia

A novel approach to construct 2-aryl/heteroaryl quinazolines was developed through an iron-catalyzed cascade reaction of 2-aminobenzyl alcohols with benzylamines under aerobic oxidative conditions. The reaction proceeds via the formation of N-benzylideneb

ABNO-Catalyzed Aerobic Oxidative Synthesis of 2-Substituted 4H-3,1-Benzoxazines and Quinazolines

A new transition-metal-free 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO) catalyzed aerobic oxidative synthesis of 2-substituted 4H-3,1-benzoxazines and quinazolines has been developed through cascade reaction of aldehydes with 2-aminobenzyl alcohols and 2-amino

Simple grinding-induced reactions of 2-aminobenzyl alcohol and benzaldehyde derivatives, a rapid synthetic route to 3,1-benzoxazines

The grinding-induced reactions of 2-aminobenzyl alcohol and benzaldehyde derivatives in the presence of 30 mol% of acetic acid to give 3,1-benzoxazines are described. The reactions were performed at room temperature affording 3,1-benzoxazines in yields above 95% and high purity when benzaldehyde and its chloro and nitro derivatives were used.

Synthesis of 2-substituted quinazolines via iridium catalysis

An iridium-catalyzed hydrogen transfer reaction was successfully applied in the synthesis of 2-substituted quinazolines in moderate yields starting from aldehydes or alcohols with 2-aminobenzylamines.

CuCl/DABCO/4-HO-TEMPO-catalyzed aerobic oxidative synthesis of 2-substituted quinazolines and 4 H -3,1-benzoxazines

The Cu/N-ligand/TEMPO catalytic system was first applied to the aerobic oxidative synthesis of heterocycles. As demonstrated, 2-substituted quinazolines and 4H-3,1-benzoxazines were synthesized efficiently from the one-pot reaction of aldehydes with 2-aminobenzylamines and 2-aminobenzyl alcohols, respectively, by employing CuCl/DABCO/4-HO-TEMPO as the catalysts and oxygen as the terminal oxidant.

Synthesis of 3h-quinazolin-4-ones and 4h-3,1-benzoxazin-4-ones via benzylic oxidation and oxidative dehydrogenation using potassium iodide-tert-butyl hydroperoxide

A simple and elegant method for benzylic activation was demonstrated employing the potassium iodide/tert-butyl hydrogen peroxide catalytic system. This methodology was further extended for the synthesis of biologically important heterocycles namely, 3H-quinazolin-4-ones and 4H-3,1-benzoxazin-4-ones including mecloqualone and etaqualone which are important quinazolinone-based drugs used for the treatment of insomnia in good yields.

Highly efficient one-pot synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines via cross dehydrogenative coupling using sodium hypochlorite

This communication describes a catalyst-free synthesis of 2-substituted quinazolines and 4H-benzo[d][1,3]oxazines using commericially available sodium hypochlorite as oxidant. Operational simplicity, mild reaction conditions and the ability to construct structurally diverse 2-quinazolines and 2-substituted 4H-benzo[d][1,3]oxazines by this method render it to be a practical alternative for the synthesis of these heterocycles.