1-NAPHTHALENE CARBAMIC

Naphthalene carbamic acid, l,2,3,4-tetrahydro-2-iodo-, methyl... 

Methylbenzimidazole, see 2-Nitroaniline Methyl 2-benzimidazole carbamate, see Benomvl Methyl benzoate, see Sulfometuron-methvl 4-Methyl-2//-l-benzopyran-2-one, see Naphthalene o-Methylbenzoquinone, see Aminocarb p-Methylbenzoquinone, see Toluene... 

Other examples of determination of the absolute configuration of bichromophoric molecules having two or more rotamers in the equilibrium include naphthalene/A -vinyl carbamate in a 1,2,3,4-tetrahydropyridine derivative123, naphthalenc/purine in deoxyadenosine adducts124-126, phenanthrene/purine in deoxyadenosine and deoxyguanosine adducts127 and pyrene/purine in adenosine adducts128. 

The nature of the aromatic substituents is apparently not critical for SSRI activity, as indicated by the structure of duloxetine (23-5), where one ring is replaced by thiophene and the other by naphthalene. The synthesis starts as above by the formation of the Mannich base (23-1) from 1-acetyl thiophene with formaldehyde and dimethyl-amine. Treatment of that intermediate with the complex from lithium aluminum hydride and the 2R,3S entantiomer of dimethylamino-l,2-diphenyl-3-methyl-butane-2-ol gives the S isomer (23-2) in high enantiomeric excess. Treatment of the aUcoxide from (23-2) and sodium hydride with 1-fluoronaphthalene leads to the displacement of halogen and thus the formation of ether (23-2). The surplus methyl group is then removed by yet another variant of the von Braun reaction that avoids the use of a base for saponifying the intermediate urethane. Thus, reaction of (23-3) with trichloroethyl formate leads to the A -demethylated chlorinated urethane (23-4). Treatment of that intermediate with zinc leads to a loss of the carbamate and the formation of the free secondary amine duloxetine (23-5) [23]. 

Since BAs occurring in food do not exhibit satisfactory absorbance or fluorescence in the visible or ultraviolet range, chemical derivatization, either pre- (35-37) or postcolumn (38), is usually used for their detection in HPLC. The most frequently employed reagents for precolumn derivatization are fluorescamine, aminoquinolyl-lV-hydroxysuccinimidyl carbamate (AQC) (39, 40), 9-fluorenylmethyl chloroformate (FMOC) (41-43), 4-dimethylaminoazobenzene-4 -sul-fonyl chloride (dabsylchloride, DBS) (44), N-acetylcysteine (NAC) (45,46), and 5-dimethyl-amino-1-naphthalene-1-sulfonyl chloride (dansylchloride, DNS) (47,48), phthalaldehyde (PA), and orf/to-phthaldialdehyde (OPA) (49-51), together with thiols such as 3-mercaptopropionic acid (MPA) (37) and 2-mercaptoethanol (ME) (35,49). 

Phenyl ureas, carbamates, organochlorine insecticides, 4-bromophenol, captan, bromo- and chloroanilines, methylanilines, bromo- and chloro-nitrobenzenes, diphenyl amino folpet, hexachlorobenzene, naphthalene, phenol, simazine... 

Scheme 31. Nickel-catalyzed O-aryl carbamate Crignard cross-coupling regiospecific access to 1,2,3- and 2,3-substituted naphthalenes.

Higher-molecular-weight amines are treated in the liquid phase usually in solvents like ethyl acetate, toluene, chlorobenzene, or chloro-naphthalene. This process is illustrated by the preparation of p-nitro-phenyl isocyanate (95%). Amine hydrochlorides or carbamic acids are sometimes used in place of the free amine. ... 

Dehydnriiahgemtwn- hydrolysis, Heathcock and Hassner used this reagent in ethanol in the completing step of the synthesis of an aziridine (4) from 1,2-dihydro-naphthalene (1) via methyl (rran.s-2-iodo-l-tctralin)carbamate (3). ... 

When the double bond of the 3-ene-l,5-diyne system is part of a benzene or a naphthalene ring, a lowered activity resulted, in agreement with the lower activity of benzo-fused enediynes already cited in Section 19.3.2. Finally, the activity both in vitro (human carcinoma KB cells) and in vivo (mice inoculated with murine P338 leukemia) of 87-89 was tested. Interestingly, while the phenyl carbamates have no detectable in vitro activity against plasmid DNA and were less cytotoxic in vitro than 87-89, an opposite behavior was observed in vivo. Thus the phenyl carbamates showed an interesting activity, while the sulfones showed little or no activity, probably due to the fact that they are quite unstable and they are not able to reach tumor cells before cycloaromatization begins. 

Fluorescence of Naphthyl Carbamate Models. Two compounds (shown below) based on carbamate substituted naphthalene will be considered as models for the naphthalene diisocyanate based polyurethanes under investigation in this paper. The propyl N-(1-naphthyl) carbamate (PNC) and dipropyl N,N -naphthalene-1,5-dlylbiscarbamate (1,5-DN3) model compounds were made by reacting the requisite mono- or diisocyanate with 1-propanol. 

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