Nucleophile nitrogen-containing

Reaction of 3-benzamido-2,5-dioxo-5,6,7,8-tetrahydro-(2ff)-l-benzopyrans 58 with nitrogen-containing nucleophiles (amines and hydrazines) provides the corresponding quinolin-2-(l//)-ones 59 <96H(43)809>. 

It is very likely, that this reaction occurs due to the equilibrium between trimethylsilyl halide and a nitrogen-containing nucleophile, which increases the electrophilicity of silyl Lewis acids. It should be noted that the configuration of stereocenters at the carbon atoms of the oxazine ring is partially distorted. Hence, it is assumed that the reaction proceeds through the intermediate cation B, which is partially isomerized into the stereoisomeric cation B through the open chain cation B". 

Many different nitrogen-containing nucleophiles can attack a carbonyl group. In this section you consider primary amines (RNH2), secondary amines (R2NH), hydroxylamine (NH2OH), and hydrazine (NH2NH2). 

Arylation at oxygen of nitrogen-containing nucleophiles by iodonium... 

Complexes of nitrogen-containing nucleophiles or silylammonium salts, [R3SiNR3]+X ... 

Ammonia and other nitrogen-containing nucleophiles react readily with internally fluorinatcd alkenes (e. g.. 28) to form products via addition-elimination sequences. The product ratio (e. g., of 29 and 30) depends strongly on the reaction conditions. 

B. Reaction of Nitrogen-Containing Nucleophiles with Aldehydes and Ketones... 

A number of reactions of nitrogen-containing nucleophiles with aldehydes and ketones involve addition of the nitrogen to the carbon of the carbonyl group, followed by elimination of water to produce a double bond. Common examples are reactions of primary amines to produce substituted imines, reactions of secondary amines to produce enamines, reactions of hydrazine or substituted hydrazines to produce hydrazones, reactions of semicarbazides to give semicarbazones, and reactions of hydroxylamine to produce oximes. Usually these reactions are run with an acid catalyst. 

Imines and substituted oximes react with several nitrogen-containing nucleophiles to provide a general synthesis of diaziridines or diazirines. ... 

The range of nucleophiles usable in this substitution reaction was very broad. Carbon nucleophiles such as acetoacetate, diethyl malonate, 3-methyl-2,4-pentanedione gave alkylated products in 98%, 94% and 86% yield, respectively. Nitrogen containing nucleophiles (hydrochloride salts of amino acids) gave Al-allylated products in 90-98% yield. Sodium phenylsulfmate and sodium azide also reacted in high yields (86% and 79%, respectively). The catalyst could be readily recovered and re-used. No loss of activity was observed over 7 continuous runs. 

Nucleophilic substitution of halogen in 2-(3)halo-3-(2)formylbenzo[ft]selenophenes by nitrogen-containing nucleophiles is the first step for the formation of new tricyclic compounds <83JHC49>. 

The fully intermolecular catalytic version was then disclosed using either sulfur- or nitrogen-containing nucleophiles (Ar-NHTs or ArS02Na) or more recently using boron terminating agents (Scheme In the latter case, it readily applies to both... 

Nucleophilic aromatic substitution reactions of haloarenes complexed to transition metal moieties with oxygen-, sulfin-, and nitrogen-containing nucleophiles allows for the synthesis of a wide variety of aryl ethers, thioethers, and amines. These metal-mediated reactions proceed under very mild conditions and allow for the incorporation of a number of different functional groups. Nucleophilic substitution reactions of chloroarenes complexed to the cyclopentadienyliron moiety have been the focus of many studies directed toward the design of functionalized organic monomers. ... 

Birch, A.J., A.J. Leipa, and G.R. Stephenson Organometallic Compounds in Organic Synthesis Some Tricarbonyl (Cyclohexadienyl) Iron Cations and Nitrogen Containing Nucleophiles. Tetrahedron Letters 3565 (1979). 

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