1-Dimethylaminonaphthalene

The 7V-methylbenzo[( e]quinoline 426 was prepared by trapping the insertion product of an internal alkyne with a tertiary dimethylamine. One methyl group is eliminated. The dimethylaminonaphthalene-Pd complex 427 is an active catalyst and other Pd compounds are inactive[290a]. 

This technique is especially useful for the preparation of a-lithio ethers, sulfides, and silanes.36 The lithium radical anions of naphthalene, 4, 4/-di-f-butyldiphenyl (DTBB) or dimethylaminonaphthalene (LDMAN) are used as the reducing agent. 

For the sulfonation step, amino acids were added as their sodium salts. The reactions were carried out in cold aqueous solution, in which the sulfonamides were immediately precipitated. By the same method dansylations of amino acids could be accomplished with N-( 1 -dimethylaminonaphthalene-5-sulfonyl)-Af -methylimidazolium chloride ... 

Substituted aziridines have been used to form homobifunctional and trifunctional crosslinking agents, although their use has been limited (Ross, 1953 Alexander, 1954). The functional group has found use, however, in the design of the fluorescent probe dansyl aziridine (5-dimethylaminonaphthalene-2-sulfonyl aziridine) (Johnson et al., 1978 Grossman et al., 1981). 

Boyle, R. (1966) The reaction of dimethyl sulfoxide and 5-dimethylaminonaphthalene-l-sulfonyl chloride./. Org. Chem. 31, 3880-3882. 

Oxosteroids, oxo bile acids 5-Dimethylaminonaphthalene-l -sulfonyl hydrazine 82, 83... 

Estradiol 5-Dimethylaminonaphthalene-l -sulfonyl chloride Lissamine rhodamine B sulfonyl chloride 87... 

Dansyl (dimethylaminonaphthalene sulfonyl) fluorophore is a good candidate as an appended fluorophore because it is very sensitive to solvent polarity (see Chapter 7). Dansyl emits strong fluorescence in a hydrophobic environment, but weak... 

Dansyl chloride (dimethylaminonaphthalene-5-sulphonyl chloride) will react with free amino groups in alkaline solution (pH 9.5-10.5) to form strongly fluorescent derivatives (Figure 10.14). This method can also be used in combination with chromatographic procedures for amino acid identification in a similar manner to the FDNB reagent but shows an approximately 100-fold increase in sensitivity. This makes it applicable to less than 1 nmol of material and more amenable for use with very small amounts of amino acids liberated after hydrolysis of peptides. The dansyl amino acids are also very resistant to hydrolysis and they can be located easily after chromatographic separation by viewing under an ultraviolet lamp see Procedure 10.1. 

Dimethylamine (109), putrescine (111), and spermidine (110), isolated from various insects (Table VIII), were obtained as p,p -nitrophenylazobenzoyl, p-phenylazobenzenesulfonyl, and I-dimethylaminonaphthalene-5-sulfonyl (dan-syl) derivatives and picrates or were detected by high-performance liquid chromatography (HPLC) using the ion-exchange resin (106,343). V,V-Dimethyl-3-phenylethylamine (131) from spiders of the genus Sclerobunus (Table VIII) has been identified by mass spectral comparison with a synthetic sample (117). 

One of the most widely used reagents for introduction of a fluorophor into primary and secondary amines is 5-dimethylaminonaphthalene-l-sulfonyl chloride, com-... 

Aldehydes, hydrazine I-Dimethylaminonaphthalene-5-sulfonyl hydrazine (dansyl hydrazine)... 

Phenols I-Dimethylaminonaphthalene-5-sulfonyl chloride (dansyl chloride)... 

Several (A/-alkenyl)iodoacetamides undergo cyclization when they are reacted with tetrakis(triphe-nylphosphine)palladium(O). The highest yields (which are generally only moderate) are obtained in DMF solution with 1,8-dimethylaminonaphthalene (Proton Sponge) to take up the hydrogen iodide formed. This reaction has been used to prepare piperidones, oxindoles, indolizidines, quinolizidines, pyrrolidines, indoles, quinolines53 and pyrrolizidines (equation 18).54... 

Although acryloyl cross-linking agents have not been common, the functional group has found use in the design of the sulfhydryl-reactive fluorescent probe 6-acryloyl-2-dimethylaminonaphthalene (acrylodan Molecular Probes) (Yem et al., 1992 Epps et al., 1992). 

---