N-Substitution

N-Substituted aminothiazoles, with R = H, Me, CHMCj, R, =H. Me-Rz = H, Me, CHMcj, Ph, and Rj, R2 = CH2CH2, have been recently obtained by condensing thioureas with 1,2-dichloroethylisothiocyanate (Scheme 131) (805). 

The reaction between the sodium salt of diethyl 2-[2-(N-substituted amino)-4-thiazolyl]malonate (298) and diethyl chloromethylenemalonate in THF at ambient temperature for 1-10 hr occurred on the central carbon atom of the malonate (298), not on the amino group, to give tetraesters (299) in 10-70% yields (86EUP168025). 

Since the chemical behavior of these unstable compounds deviated in many respects from that of the arylamines, it was first thought that they preferably exist in the imino form 257. In 1960 <1960AK515>, it was proved by NMR spectroscopy that the parent aminothiophene occurs exclusively in the amino form 256. This was confirmed later by more detailed investigations <1967TL5201, 1969JHC147>. Several other 2-N-substituted thiophenes have been... 

Fig. 7 General structme of 4-alkyl/aryl-2-(N-substituted aminoalkylamido) thiazoles associated with nitric oxide (NO) and glycosaminoglycans (GAGs) release inhibition...

A different series of 4-alkyl/aryl-2-(N-substituted aminoalkylamido) thiazoles (Fig. 8, Table 6) were analyzed by Litina et al. for their antiinflammatory activity in terms of the inhibition of carrageenan mice paw edema (%CPE) [90]. hi this study the activity (%CPE) was correlated with several physicochemical and indicator parameters of these compounds (Table 6) [91]. 

Asymmetric syntheses based on chiral diamines. Optically active secondary alcohols are obtained by reduction of prochiral ketones with the chiral hydride reagent 1 prepared from lithium aluminium hydride and ( )-2-(N-substituted aminomethyl)-... 

The analogous chemistry of 2-N-substituted 1,2,3-triazoles has been reported by Riebsomer and his collaborators - starting with 2-phenyl-4-D-glucosotriazole (4.2-3) and potassium permanganate (Eq. 23). The subsequent conversions to acid chloride, esters, and amides were made in good to... 

Wirth and coworkers published in 2007 a detailed study of the aziridination of alkenes with the PhI(OAc)2/N-substituted hydrazine system (Scheme 4.17) and, in particular, reported tentative evidence that this reaction proceeds through the formation of an aminoiodane that reacts directly with the alkene [44]. 

Brown, D. and Keeler, R. F. (1978b). Structure-activity relation of steroid teratogens. 2. N-Substituted jervines, J. Agric. Food Chem., 26 564-566. 

The yc(inner carbon)Pt Coupling of 983 zb 7 Hz and yc(outer carbon)Pt 32.5 0.7 Hz, observed by Wang et in the spectra of three novel Pt(ii) 2-N substituted N-confused porphyrines, (2-aza-2-benzylo3Q carbonyl-methyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N//, N")platinum(ii), (2-aza-2-p-cyanobenzyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-iV,iV, N")platinum(ii) and (2-aza-2-ptrifluoromethylbenzyl-5,10,15,20-tetraphenyl-21-carbaporphyrinato-N,iV, iV")platinum(ii) have been used by the authors as the proof that the Pt atom in the studied compounds is coordinated to three nitrogen atoms and to the unsubstituted p-carbon atom of the pyrrole ring. 

N-Substituted Purines with Non-coordinating Pendant Arms. 149... 

Equimolar quantities of acetylenedicarboxylic acid esters (166) and 2-N-substituted l,3-dithiolan-2-imines (169) undergo a 1,3-dipolar cycloaddition, with elimination of ethylene, to yield A -thiazoline-2-thiones (168). The same products result from 2-alkylthio-l,3,4-thiadiazoline-5-thiones (167), with loss of alkyl thiocyanate as shown. They are desulphurized to the corresponding thiazolinones (172) by the action of mercuric acetate in acetone-acetic acid. They react with two further moles of the acetylenic reagent (166) to produce the spiranes (170 e.g. = R = COzMe), which are in turn desulphurized and cleaved by Raney nickel to the AMhiazoline derivatives (171). An analogous series of reactions was carried out using propiolic acid esters. ... 

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