3-Acylamino-5-methyl

Examples include the synthesis of 3-amino-l,2,4-oxadiazoles starting from 3-acylamino-5-methyl-l,2,4-oxadiazole <2002H811> and 2-aryl-l,2,3-triazoles from l,2,4-oxadiazole-3-ketone arylhydrazones <1999T12885, 2006JOC5616>. Oximes, hydrazones, formamidines, and thioureas of the furazan series also undergo base-catalyzed mononuclear rearrangements <2004RCB1121>. Nucleophilic attack at N(3) takes place in the benzofuroxan series. For example, reaction with secondary amines leads to o-nitroarylhydrazines (Scheme 55). 

Katritzky, A.R., Zhang, G., and Jiang, J., Convenient preparations of diethyl [(acylamino)methyl]phosphonates, 2-azabutadienes, and isoquinolines from a 1,2-monoazabisylide equivalent,. Org. Chem., 59, 4556, 1994. 

The bromocyclization of A/,jV-dialkylaminomethyl ethers of allyl and propargyl alcohols to form oxa-zolidinium salts has been reported, but not used in synthesis.255 The heterocyclization of /V-acylamino-methyl ethers with mercury salts has been used for stereoselective synthesis of a variety of 1,2-amino alcohol systems. These cyclizations form rans-4,5-dialkyl oxazolidine products with good to excellent stereoselectivities (equation 120 and Table 33). As shown by entry 5, 6-endo cyclization predominates (6 3) with an internal double bond of ( )-configuration, but this mode of cyclization is reduced with substrates containing a (Z) double bond and/or allylic oxygen substitution (Table 33, entries 6-9). 

Tifluadom is a 2-[(acylamino)methyl]-l,4-benzodiazepine (Fig. 8), with K-agonist and cholecystokinin-A (CCK-A) antagonist abilities [29]. Cappelli and colleagues successfully discriminated KORs from CCKs, and KORs from MORs using the 2-[(acylamino)ethyl] derivatives [29, 31]. Although tifluadom is a racemic... 

C2N2S s N N — — 5-Acylamino-3-methyl-l,2,3-thiadiazole 5-phenyl-l,2,3-thiadiazole 3-oxide... 

Furan, 3-acetyl-5-(hydroxymethyl)-2-methyl-synthesis, 4, 663 Furan, 2-acyl-synthesis, 4, 148, 690 Furan, 3-acyl-synthesis, 4, 662, 670 Furan, 4-acyl-2-alkyl-synthesis, 4, 688 Furan, 3-acylamino-tautomerism, 4, 38... 

Thiazole, 2-acetylamino-4-methyl-alkylation, 6, 256 Thiazole, 2-acylamino-4-hydroxy-synthesis, 6, 297 Thiazole, 5-alkoxy-cleavage, 6, 289 synthesis, 6, 302 Thiazole, 2-alkyl-A7-alkylation, 6, 253 hydrogen exchange, 6, 276 methylation, 6, 253 quatemization, 6, 253-254 reactions, S, 88 Thiazole, 4-alkyl-A7-alkylation, 6, 253 methylation, 6, 253 quatemization, 6, 253-254 Thiazole, 5-alkyl-A7-alkylation, 6, 253 methylation, 6, 253 Thiazole, 2-alkylamino-tautomerism, 6, 248 Thiazole, 4-alkyl-2,5-dimethyl-quatemization, 6, 253-254 Thiazole, 2-alkylthio-reactions, S, 103 rearrangement, 5, 103 6, 291 Thiazole, 3-allyl-4-hydroxy-2-imino-synthesis, 6, 297 Thiazole, 2-allyloxy-rearrangement, 6, 289 Thiazole, 2-amino-diazo coupling, 6, 257 nitration, 6, 255... 

The aforementioned exception and the rather limited experimental material available do not allow any conclusions about the general applicability of the Hammett equation, using the same a- and p-values as for benzenes, to be drawn with certainty. The present author has pointed out that large deviations should be expected with strong - -M-substituents, as is also indicated from the rates of alkaline hydrolysis of methyl 5-amino- and 5-acylamino-2-thenoates. From the chemical shifts in the NMR spectra of thiophenes and benzenes it appears that another set of cr-values should be used in the thiophenes series which seems plausible since the transmission of the sub-... 

Some substituents such as the acylamino group are readily decomposed by many nucleophiles to give a poorer leaving group (e.g., amino). Others, such as nitroamino and sulfonylamino, are less reactive when they are anionized by the nucleophile. 3-Nitroamino-pyridazine (117) and its 6-methyl derivative are readily aminated with benzylamine (130°, short time ). 4,6-Dimethyl- and 6-methyl-2-nitroaminopyrimidine undergo 2-substitution on warming a few minutes with hydroxylamine, hydrazine, primary or secondary alkylamines, or anilines. 

Acetamino-methyl- -athylester-nitril 206 Acylamino- -diathylester 203 Acyl- -diathylester... 

Acylamino-3-acyloxymethyl-2-carboxy- 516 7-Acylamino-3-methoxymethyl-2-carboxy- 516 7-Amino-6-oxo-3-acetoxymethyl-4-carboxy- 631 7-(5-Carboxy-pentanoylamino)-6-oxo-3-acctoxy-methyl-4-carboxy- 631... 

A general synthetic route to meso-ionic iV-acyl-l,3-thiazol-5-imines (108, R = Ph, = Me, R = Me or Ph, R = COPh) is provided by treatment of thiobenzamidoaminoacetonitriles, Ph-CS-NMe-CHR-CN, first with benzoyl chloride and then with aqueous alkali. Alternatively, the thiobenzamidoaminoacetonitriles and hydrogen chloride give the corresponding salts, which with benzoyl chloride and aqueous alkali give -acyl l,3-thiazol-5-imines Derivatives (108, R = SMe) have been obtained by treating 5-acylamino-4-thiazoline-2-thiones with methyl iodide and aqueous alkali. ... 

Other novel diazo compounds that have been subjected to 1,3-dipolar cycloaddition with activated alkenes, and that give unusually functionalized pyrazolines (Scheme 8.7), include l-diazo-3-trimethylsilylpropan-2-one (20) (49), 2-diazo-methyl-4(57/)-furanones (21) (50), methyl 2-diazo-5-methylanilino-5-oxopentano-ate (22) (51), 2-(acylamino)-2-diazoacetates (23) (51), ethyl 2-diazo-4,4,4-trichloro-3-(ethoxycarbonylamino)butyrate (24) (52), and diazopropyne (53). 

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