54722-74-6

Usage

Uses

1,2-Oxazinane Hydrochloride is used for synthesis of α''-?amino-?α,?β-?ynones.

Upstream product

• 54463-32-0 N-ethoxycarbonyltetrahydro-1,2-oxazine 
• 664364-75-4 tert-butyl 1,2-oxazinane-2-carboxylate 

Downstream Products

• 92020-90-1 1-(4-chloro-phenyl)-3-[1,2]oxazinan-2-yl-propan-1-one 
• 40548-68-3 N-nitrosotetrahydro-1,2-oxazine 
• 26893-65-2 (1,2-oxazinan-2-yl)(phenyl)methanone 
• 1352201-97-8 (2S)-2-amino-3-(4-hydroxy-3-nitrophenyl)-1-(1,2-oxazinan-2-yl)propan-1-one, trifluoroacetic acid salt 
• 1352201-93-4 (2S,3S)-2-amino-1-(1,2-oxazinan-2-yl)-3-phenylbutan-1-one, trifluoroacetic acid salt 
• 125794-28-7 C₆H₁₀ClNO₂ 

Relevant academic research and scientific papers

The Application of 1,2-Oxazinanes as Chiral Cyclic Weinreb Amide-Type Auxiliaries Leading to a Three-Component, One-Pot Reaction

1,2-Oxazines were synthesised via a copper-catalysed aerobic acyl nitroso Diels-Alder reaction from 1,4-disubstituted 1,3-dienes and N-Boc-hydroxylamine. From this, 1,2-oxazinanes were obtained in a novel follow-up reaction path. The stability of several 1,2-oxazines and 1,2-oxazinanes towards organometallic compounds was tested to rate their operability as cyclic chiral Weinreb amide auxiliaries. 3,6-Di-tertbutyl-1,2-oxazinane gave the best results and was introduced as a chiral Weinreb amide-type auxiliary to yield chiral α-substituted ketones in a diastereomeric ratio of up to 98:2. The removal of the auxiliary can be performed with BuLi to form unsymmetrical α-chiral ketones. Thereafter, the chiral auxiliary can be re-isolated and purified by sublimation under vacuum.

Macrocyclic compounds and methods for their production

There is provided inter alia compounds of formula (I): for use in treatment of viral infection or as an immunosuppressant.

FUSED BENZENE DERIVATIVE AND USE

The present invention provides a compound represented by the general formula: [wherein Ring A represents an optionally substituted 5- to 8-membered ring, Ring B represents a further optionally substituted 4- to 10-membered ring, Ring C represents a further optionally substituted benzene ring, X1 represents carbon atom, X2 represents a carbon atom, an oxygen atom, etc., W represents a nitrogen atom, etc., Y11 represents a group represented by the formula CR2R3' (wherein R2 represents a hydrogen atom, a cyano group, a nitro group, etc., and R3' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), Y21 represents a group represented by the formula CR4R5' (wherein R4 represents a hydrogen atom, a cyano group, a nitro group, etc., and R5' represents a hydrogen atom, a cyano group, a nitro group, etc., respectively), etc., and R1 represents an electron-withdrawing group, respectively. The formula represents a single bond or a double bond] or a salt thereof, which is useful as an androgen receptor modulator.

N-nitroso-N,O-dialkylhydroxylamines: Preparation, structure, and mechanism of the hydronium ion catalysed solvolytic nitrous oxide extrusion reaction

Eleven N-nitroso-N,O-dialkylhydroxylamines, RN(NO)OR′, have been prepared and the mechanisms of their hydronium ion catalysed solvolyses in aqueous solution which liberate nitrous oxide have been investigated. All reactions are first-order in substrate and first-order in hydronium ion, and the second-order rate constants at 25°C vary over a range of less than 140 in spite of considerable variation in substrate structure (R ranges from methyl to 4-methoxybenzyl to 2-adamantyl, for example) and changes in solvent composition (water with up to 50% methanol or 66% acetonitrile). Enthalpies and entropies of activation are qualitatively similar throughout the range (ΔH?= 72-93 kJ mol-1 and ΔS? = -19 to -57 J K-1 mol-1) which, with the product analyses, are accommodated by a mechanism involving pre-equilibrium protonation of the substrates followed by rate-limiting dissociation to give RN2O+ and HOR′. The oxodiazonium ion intermediate, RN2O+, then dissociates further to give the carbenium ion intermediate, R+, or suffers direct nucleophilic displacement of N2O by solvent (the external nucleophile) or by R′OH (the internal nucleophile liberated in the initial fragmentation). The carbenium ion, R+ (if formed), suffers nucleophilic capture either by solvent or by R′OH. When acetonitrile is the co-solvent (rather than methanol) for the N-(2-adamantyl) substrate 3g, the product of the Ritter reaction, 2-acetamidoadamantane, is detected. These nitrous oxide liberating reactions are compared with the nitric oxide liberating reactions of related N-nitrosohydroxylamines, and the origin of the difference between them is identified. The N(1)-nitroso group in the N,O-dibenzyl compound 3c is shown by X-ray crystallography to be essentially coplanar with the C and O atoms also bonded to N(1).