Optimization of HNO Production from N,O-bis-Acylated Hydroxylamine Derivatives
摘要:
A wide range of N,O-bis-acylated hydroxylamine derivatives with chloro or arenesulfonyl leaving groups, and a related set of N-hydroxy-N-acylsulfonamides, have been synthesized and evaluated for nitroxyl (HNO) production. Mechanistic studies have revealed that the observed aqueous chemistry is more complicated than originally anticipated, and have been used to develop a new series of efficient HNO precursors (4u-4x, 7c-7d) with tunable half-lives.
The synthesis and some reactions of N-hydroxycarbamates
作者:E. Boyland、R. Nery
DOI:10.1039/j39660000346
日期:——
chloroformate, gave N-hydroxy-N-phenylurethane. Hydroxylamine hydrochloride and ethyl chloroformate yielded a product which changed into hydroxyurethane. Alkyl N-hydroxycarbamates and hydroxyurea gave O-xanthydryl derivatives. The N-hydroxycarbamates with aqueous dipotassium tetracyanonickelate(II) formed dipotassium tricyanonitrosylnickelate(II). No evidence of a Lossen-type rearrangement during the acid
羟胺和氯甲酸烷基酯在碱性介质中反应,以形成ñ - , - NO -二- ,和NNO -三烷氧羰基羟胺,依次。N-甲基羟胺类似地得到N-和NO-二烷氧基羰基-N-甲基-羟胺,O-甲基羟胺产生N-和NN-二烷氧基羰基-O-甲基羟胺。N-苯基羟胺与1当量的氯甲酸乙酯反应,得到N-羟基-N-苯基氨基甲酸酯。盐酸羟胺和氯甲酸乙酯产生产物,其变为羟基氨基甲酸酯。N-羟基氨基甲酸酯烷基和羟基脲得到O-黄羟基衍生物。所述Ñ -hydroxycarbamates用含水四氰二钾(II)而形成二钾tricyanonitrosylnickelate(II)。在这些羟氨基衍生物的酸和碱水解过程中,没有证据表明发生了洛森型重排。讨论了可能的水解机理。
Hydroxyaminohydrocarbonphosphonic acid derivatives and use thereof as an
申请人:Fujisawa Pharmaceutical Co., Ltd.
公开号:US04182758A1
公开(公告)日:1980-01-08
Hydroxyaminohydrocarbonphosphonic acid derivatives represented by the formula: ##STR1## wherein R.sup.1 is hydrogen or acyl, R.sup.2 is hydrogen, lower alkyl, ar(lower) alkyl or acyl, and A is lower alkylene, lower alkenylene or hydroxy(lower) alkylene, or the esters at the phosphono group thereof or the pharmaceutically acceptable salts thereof, excepting 3-(N-acetyl-N-hydroxyamino) propylphosphonic acid, 3-(N-acetyl-N-hydroxyamino)-2-hydroxypropylphosphonic acid, and their pharmaceutically acceptable salts, and processes for preparing the same. Included are compounds having antimicrobial activity against various pathogenic organisms.
New hydroxyaminohydrocarbonphosphonic acid derivatives of the formula: ##STR1## wherein R.sup.1 is hydrogen or acyl, R.sup.2 is hydrogen, lower alkyl, ar(lower)alkyl or acyl, and A is lower alkylene, lower alkenylene or hydroxy(lower)alkylene, or the esters at the phosphono group thereof or the pharmaceutical acceptable salt thereof, and production and use thereof.
The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.