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1,3-Thiazol 2-Amino-5- -4-phenyl

The crystal and molecular structures of 2-amino-4-phenylthiazole hydrobromide have been determined by radiocrystallography the angle between the thiazole and phenyl rings was found to be 19 . The major features are reported in Fig. VI-4 (142). [Pg.29]

The preparation of 5-azothiazoles uses the nucleophilic character of C-5 carbon in reaction with the appropriate diazonium salt (402, 586). These 5-azothia2oles form 1 1 complexes with Ag (587). 2-Amino-4-methyl-5-arylazothiazoles give reduction waves involving two-electron transfer the Ej/ values correlate to the angle between the thiazole and phenyl rings (588). [Pg.108]

Aus l,3-Thiazolio[3,2-c]pyrimidinium-olalen bzw. Salzen entstehen bei der hydrolytischen Ringoffnung 1,3-Thiazole, die in 2-Position einen 2-Amino-phenyl-Substituenten tragen z.B. ... [Pg.235]

Zur Arbeitsvorschrift zur Herstellung von 2-Amino-5-(4-amino-phenyl)-1,3-thiazol s. Bd. X/2, S. 738f. [Pg.258]

The 2-(alkylimino)-3-amino -phenyl-2,3-dihydro-l,3-thiazol-3-amines 319 behave similarly and undergo ring expansion on heating with concentrated hydrochloric acid to give the 1,3,4-thiadiazines 318. The 1,3-thiazole derivative 320 also undergoes a ring expansion to the 1,3,4-thiadiazine 321 by treatment with FeCls in DMF (Equation 52) <1996KGS1424>. [Pg.442]

Further products prepared by the thionyl chloride method in solution are Dolastatin, a thiazole amino acid component (gln)Thz (70% yield) [1110], 4-phenyl-3-furoxanecarbonitrile (55% yield) [1111], ethyl 5-cyano-l-(l,l-dimethyl-ethyl)-lH-pyrazolo-4-carboxylate (61% yield) [1112], ethyl 2-anilino-4-chloro-5-cya-nothiophene-3-carboxylate (77% yield) [1113], and 4-cyanoisoxazole from its oxime tosylate (47% yield) [1114]. [Pg.380]

Reaction between 2-chIoronicotinic acid (130) and 2-amino-4-phenyl-thiazole furnishes 3-phenyl-5-H-pyrido[2,3,-d]thiazolo[3.2-fl]pyximidin-5-one (131) (Scheme 86) (293). This reaction was extended to other pyridinyl compounds (294). [Pg.57]

Acetamidothiazole is nitrated in the same way (58, 378, 379). 2-Acetamido-4-phenylthiazole is reported to be nitrated on C-5 (380) as opposed to 2-amino-4-phenylthiazole, where nitration occurs on the phenyl ring (381). This latter result is not consistent with the other data on electrophilic reactivity in most cases 2-amino-4-arylthiazole derivatives react with electrophilic reagents at the C-5 position (see Sections rV.l.B and D). Furthermore, N-pyridy]-(2)-thiazolyl-2-amine (178) is exclusively nitrated on the thiazole ring (Scheme 113) (132, 382). [Pg.72]

The general pattern of alkylation of 2-acylaininothiazoles parallels that of 2-aminothia2ole itself (see Section III.l). In neutral medium attack occurs on the ring nitrogen, and in alkaline medium a mixture of N-ring and N-amino alkylation takes place (40, 43, 161. 163). In acidic medium unusual behavior has been reported (477) 2-acetamido-4-substituted thiazoles react with acetic anhydride in the presence of sulfuric acid to yield 2-acetylimino-3-acetyl-4-phenyl-4-thiazolines (255) when R = Ph. but when R4 = Me or H no acetylation occurs (Scheme 151). The explanation rests perhaps in an acid-catalyzed heterocyclization with an acetylation on the open-chain compound (253), this compound being stabilized... [Pg.91]

An interesting set of central nervous system properties has also been discovered and studied (Table VI-10). The work devoted to piscaine must be emphasized besides finding hypnotic properties of 2-amino-4-phenyl-thiazole on fish, the authors studied the structure of the metabolite, as well as the localization of the (radio labeled) metabolic product in various organs. Recently, thiazol-4-yl methoxyamine was shown to inhibit the development of morphine tolerance (1607). 5-Aminothiazole derivatives such as 419a were proposed as cardiovascular agents (1608, 1610). Substitution of the 5-aminothiazole radical on the cephalophosphorin structure gives a series of antibacterial products (1609). [Pg.138]

Beyond pharmaceutical screening activity developed on aminothiazoles derivatives, some studies at the molecular level were performed. Thus 2-aminothiazole was shown to inhibit thiamine biosynthesis (941). Nrridazole (419) affects iron metabohsm (850). The dehydrase for 5-aminolevulinic acid of mouse liver is inhibited by 2-amino-4-(iS-hydroxy-ethyl)thiazole (420) (942) (Scheme 239). l-Phenyl-3-(2-thiazolyl)thiourea (421) is a dopamine fS-hydroxylase inhibitor (943). Compound 422 inhibits the enzyme activity of 3, 5 -nucleotide phosphodiesterase (944). The oxalate salt of 423, an analog of levamisole 424 (945) (Scheme 240),... [Pg.152]

The action of ammonia on N-(aryl-i,3-oxathiol-2-ylidine) tertiary im-inium salts (254) yields linear intermediates (255) that cyclize to 2-amino-4-phenyl thiazoles (256) on crystallization from acetic acid (Scheme 129) (730). [Pg.300]

The A-acetyl derivatives of the 2-alkylthio-l,3-thiadiazol-4-imines (124, R = SR, R = Ac) undergo nucleophilic displacement reaction with amines (benzylamine, cyclohexylamine, morpholine, or aniline) giving the 2-amino derivatives (124, R = NRj, R = Ac). The salt (126, R = R = Ph, R = R = H, X = Cl) reacts with aniline at room temperature giving 4-anilino-2-phenyl-l,3-thiazole (128), presumably by a mechanism involving cleavage of the heterocyclic ring. ... [Pg.29]

Thiazoles, vinyl-radical polymerization, 6, 278 Thiazole-5-sulfonic acid, 2-amino-synthesis, 6, 255-256 Thiazole-2-sulfonic acids reactions, 5, 104 6, 291 Thiazole-5-sulfonic acids synthesis, 6, 255 Thiazole-5-thione, 2-phenyl-tautomerism, 6, 249 Thiazolethiones reactivity, 6, 250 Thi azole-2-thiones reactions, 5, 102 tautomerism, 5, 367 Thiazolidine, 2-alkyl-occurrence, 6, 327 Thiazolidine, 2-arylimino-X-ray analysis, 6, 238 Thiazolidine, 4-imino-mesoionic didehydro derivative nomenclature, 1, 34 nomenclature, 1, 34... [Pg.874]

The addition of DMAD to 2-aminothiazole (25) gave 26, whereas propiolic ester gave 27, 28 and 29, all derived by Michael-type additions.549 Dunwell and Evans550,551 have also added acetylenic esters to 2-amino- (and 2-amino-4-methyl)thiazole and obtained 26 and 27 from DMAD and EP, and similar compounds from tetrolic and phenyl-propiolic esters. By independent synthesis, these compounds were shown not to have the isomeric structures derived by initial addition to the exocyclic nitrogen. [Pg.454]

Reaction of 2-amino-4-phenylthiazole with one equivalent of nitric acid in sulfuric acid at 3 to 5°C results in a mixture of products containing 2-amino-4-(4-nitrophenyl), 2-amino-5-nitro-4-(4-nitro-phenyl), and a small amount of 2-amino-5-nitro-4-phenylthiazole. Work-up of the reaction mixture after only 10 min gives the same products but in different proportions. The use of two equivalents of nitric acid produces about 90% of 2-amino-5-nitro-4-(4-nitrophenyl)thiazole (59JOC187). [Pg.242]


See other pages where 1,3-Thiazol 2-Amino-5- -4-phenyl is mentioned: [Pg.964]    [Pg.956]    [Pg.1123]    [Pg.20]    [Pg.572]    [Pg.122]    [Pg.877]    [Pg.248]    [Pg.274]    [Pg.133]    [Pg.92]    [Pg.103]    [Pg.253]    [Pg.40]    [Pg.184]    [Pg.122]    [Pg.877]    [Pg.248]    [Pg.233]    [Pg.236]    [Pg.240]    [Pg.241]    [Pg.413]    [Pg.17]   
See also in sourсe #XX -- [ Pg.4 , Pg.40 ]




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2-Amino-4 thiazole

2-Amino-4- thiazoles

4-phenyl-5- thiazole

5-Amino-2- -4-phenyl

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