709-25-1

Upstream product

• 98-88-4 benzoyl chloride 
• 2878-14-0 2-methylallylamin 
• 19312-06-2 4,5-dihydro-4,4-dimethyl-2-phenoxazole 
• 67-56-1 methanol 
• 21384-58-7 2,2-dimethylaziridin-1-yl-phenylmethanone 
• 86-29-3 Diphenylacetonitrile 
• 108-98-5 thiophenol 
• 91-20-3 naphthalene 
• 519-73-3 triphenylmethane 
• 64-19-7 acetic acid 
• 120-12-7 anthracene 
• 65-85-0 benzoic acid 
• 1663-39-4 tert-Butyl acrylate 
• 2719-27-9 cyclohexanylcarbonyl chloride 

Downstream Products

• 33561-48-7 5,5-dimethyl-2-phenyl-4,5-dihydrooxazole 
• 115859-59-1 1-benzoyl-2-hydroxy-4-methylpyrrolidine 
• 115859-57-9 1-benzoyl-2-formyl-4-methylpyrrolidine 
• 2901-80-6 N-benzoyl-D,L-valine 
• 133523-77-0 5-methyl-2-phenyl-5-((phenylselanyl)methyl)-4,5-dihydrooxazole 
• 133523-73-6 N-(2-methylallyl)benzothioamide 
• 113261-11-3 5-methyl-2-phenyl-5-phenylthiomethyl-4,5-dihydro-1,3-oxazole 
• 113261-12-4 5-methyl-2-phenyl-5-propylthiomethyl-4,5-dihydro-1,3-oxazole 
• 5202-81-3 N-(2-methyl-1-propen-1-yl)benzamide 
• 37950-61-1 5,5-Dimethyl-2-phenyl-thiazoline 
• 14599-03-2 methyl 2-benzamido-3-methylbutanoate 
• 133523-70-3 5,6-dihydro-5-methyl-2-phenyl-4H-1,3-thiazine 
• 133523-83-8 5-Methyl-2-phenyl-5-phenylselanylmethyl-4,5-dihydro-thiazole 
• 137521-30-3 3-methyl-4-(benzoylamino)butanol 

Relevant academic research and scientific papers

Electrochemical oxidative cyclization of: N -allylcarboxamides: Efficient synthesis of halogenated oxazolines

Herein, we reported an efficient and sustainable intramolecular electrochemical cyclization of N-allylcarboxamides for the synthesis of various halogenated oxazolines. This method was conducted in a simple undivided cell by employing lithium halogen salts

Stereoselective Oxidative Cyclization ofN-Allyl Benzamides to Oxaz(ol)ines

This study presents an enantioselective oxidative cyclization ofN-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besidesN-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates, giving rise to a plethora of chiral 5-memberedN-heterocycles. By applying a multitude of further functionalizations, we finally demonstrate the high value of the observed chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.

Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex

We report the development of a new aminoxyl radical catalyst, CHAMPO, for the electrochemical diazidation of alkenes. Mediated by an anodically generated charge-transfer complex in the form of CHAMPO-N3, radical diazidation was achieved across a broad scope of alkenes without the need for a transition metal catalyst or a chemical oxidant. Mechanistic data support a dual catalytic role for the aminoxyl serving as both a single-electron oxidant and a radical group transfer agent.

Radical Redox-Relay Catalysis: Formal [3+2] Cycloaddition of N-Acylaziridines and Alkenes

We report Ti-catalyzed radical formal [3+2] cycloadditions of N-acylaziridines and alkenes. This method provides an efficient approach to the synthesis of pyrrolidines, structural units prevalent in bioactive compounds and organocatalysts, from readily available starting materials. The overall redox-neutral reaction was achieved via a redox-relay mechanism, which harnesses radical intermediates for selective C - N bond cleavage and formation.

Copper-Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes

Most of the precedent copper-catalyzed trifluoromethylation reactions of unactivated alkenes concern terminal alkenes, and these processes are terminated in elimination, or nucleophilic addition, or semipinacol rearrangement, or C-H bond functionalization steps. In this study, we develop a trifluoromethylation method for both unactivated terminal and internal alkenes to enable divergent late-stage radical cyclization and achieve high molecular complexity. These cyclizations are well consistent with Baldwin's rule. Furthermore, a kinetic isotope effect (KIE) study and control reactions were conducted, and a plausible mechanism is proposed.

Experimental and theoretical rearrangement of N-acyl-2,2- dimethylaziridines in acidic medium

The acid isomerization of N-acyl-2,2-dimethylaziridines 1 in concentrated sulfuric acid at room temperature leads to oxazolines 2 but the neutral hydrolysis of 1 in pure water at room temperature leads to amidoalcohols 3. However, the use of aqueous solutions of H2SO4 at different concentrations at room temperature leads to a mixture of oxazolines 2, amidoalcohols 3 and allylamides 4 with yields depending on the acidity of the medium and the nature of the acyl group. A mechanism has been suggested to explain the formation of these three products. DFT calculations employing the Gaussian 09 program with DFT/B3LYP methods and 6-311++G(2d,2p) basis set were carried out which gave the most stable geometry as well as their atomic charge distributions of compounds 1-4. [Figure not available: see fulltext.]

Isomerisation catalysee par le gel de silice et L'argile activee de N-Acyl-2,2-Dimethylaziridines: Approche mecanistique

Silica gel and activated clay, behaving as Lewis acids, reacted with N-acyl-2,2-dimethylaziridines 1 to lead to pentacoordinated aziridinium silicate ions. The regiospecific ring opening on the CMe2 carbon side of the intermediate I involves, after remova

Aziridines. 76: Neglected aspects of anthracenide (anthracenidyl) chemistry - Reactions with two N-benzoylaziridines

Reaction of anthracenide A.- with N-benzoylaziridines 1a,b forms charged radicals 3a,b by single electron transfer and homolytic ring opening. Reactions follow that are known or expected as e.g. coupling with position 9 of A.- forming dihydroanthracene anions 9a,b that yield amidoethylated dihydroanthracenes 10a,b, or react with 1a,b giving finally 9,10-bis-amidoethylated dihydroanthracenes 11a,b. Results depend on experimental conditions and on the counter ions Na+ or Li+. Coupling is not regiospecific: contributions by positions 2 and 1 reach 29% or 4%, respectively, of total coupling with the primary radical 3a; much higher contributions are possible with Li. Product 21s (probably 3,3′-disubstituted tetrahydrobianthryl) may arise by hydrogen detachment from the first intermediate (29) of coupling with position 2 and dimerization of the formed 2-substituted A.- (30). Coupling products may be fully aromatized or may be hydroxylated in one of the benzylic positions. With counter ion Li+ a non-SET reaction of 1a with the dimer of A.- is indicated by the isolation of 9-benzoyl-dihydroanthracene 15 and by 19% yield of 16a (aromatized 10a). Reaction of 3b with anthracene is indicated by 10,10′-disubstituted tetrahydrobianthryl 37. Wiley-VCH Verlag GmbH, 2000.

Competition in the sodium iodide catalysed isomerisation of some aziridines

N-Acyl-2,2-dimethylaziridines have been shown to be isomerised by sodium iodide info three isomers. The yield of these isomers appears to depend on the electronic effect of the acyl group.

Reactions of N-acylaziridines with sodium metal and sodium naphthalenide. Elimination of olefines

Reactions of N-acylaziridines 1a-g (N-benzoyl except 1d) with sodium or naphthalenide N.- in THF provide a variety of products that usually arise via the aziridino ketyls 2. Homolytic ring opening of 2 generates the amidatoalkyl radicals 3. Only with a very short reaction time were small amounts of benzil or benzoylnaphthalenes obtained indicating a reversible trapping of 2 by dimerization or coupling with N.-. Homolysis of 2 produced always the more stable 3 apart from reactions of monomethylaziridines 1c,d where the primary radical i-3c,d is kinetically favoured. The amides R1CONHCHR4CHR2R3 (9, isopropylamides i-9c,d from 1c,d) were usually the main products. 9 arise from 3 either by H atom abstraction from THF (probably in sodium metal runs) or by reduction of 3 to carbanions 5 that abstract a proton from THF (N.- runs). Addition of 5a (R2-4 = H) to 1a gives finally the ketone 8a. Self reaction of primary radical 3a is dimerization. Self reaction of tertiary or secondary radicals is disproportionation when an allylamide arises. This isomerizes to an enamide unless it is conjugated. R2R3C=CHR4 and R1CONH2 arise (probably) always. The mechanism, possibly a cyclic process of anion 6, is not clear. Johann Ambrosius Barth 1996.