5-phenyl-3- -1,2,4-triazine

The photochemistry of 5-phenyl-l,2,4-thiadiazole 12 is more complicated. Irradiation of compound 12 also gave benzonitrile (58%) along with 3-phenyl-l,2,3-thiadiazole H (18%), phenyl-1,3,5-triazine 13 (4%), diphenyl-1,3,5-triazine 14 (2%), and 3,5-diphenyl-l,2,4-thiadiazole 15 (trace). 3-Methyl-5-phenyl-l,2,4-thiadiazole, when irradiated, affords a similar distribution of compounds. 1SN labeling studies suggested the mechanisms of the transformations all proceed via a common intermediate 16 (Equation 1) <2003JOC4855>. 

Furthermore, it was pointed out that, whereas the formation of the amino adduct is fast and the formation of the product slow, it is possible that an equilibrium exists among the starting materials, their 1 1 a-amino adducts, and their open-chain amidines (Scheme 11.54). When this is the case, one may expect that, if the amination of phenyl-1,3,5-triazine is stopped before complete conversion, the retrieved starting material should be N-labeled. This has indeed been found. This behavior is in agreement with that observed with the Chichibabin amination of 4- and 5-phenylpyrimidine. 

Simig, G., Van der Plas, H. C. The SN(ANRORC) mechanism. XVII. An SN(ANRORC) mechanism in the amination of phenyl-1,3,5-triazine with potassium amide in liquid ammonia. A novel mechanism for the Chichibabin reaction. Red. Trav. Chim. Pays-Bas 1976, 95,125-126. 

The ANRORC mechanism was first observed upon amination of phenyl-1,3,5-triazine (26) with potassium amide in liquid ammonia (76RTC125). When 26 was treated with excess potassium amide in liquid ammonia at -33°C for 40 hr, a low yield (9%) of 4-amino-2-phenyl-l,3,5-triazine (27)... 

Substituted triazines have been subjected to amination with potassium amide in liquid ammonia. With 2,4-diphenyl-l,3,5-triazine (260), treatment with potassium amide in liquid ammonia afforded a typical Chichibabin product, 2-amino-4,6-diphenyl-I,3,5-triazine (261) (Scheme 89) (76RTC 113). Through labeling experiments, it was established that the amination was not occurring via an Sn(ANRORC) mechanism, but rather by an Sn(AE) process. However, Sn(ANRORC) does occur during the amination of phenyl-1,3,5-triazine, and this has been elaborated upon in Section II,B,1. 

SCHEME 17.2 Simplified deactivation scheme and ESIPT for a 2-(2 -hydroxy-phenyl)-1,3,5-triazine [11]. 

CAS 91-76-9 23844-24-8 EINECS/ELINCS 202-095-6 Synonyms Benzochinamide Benzquinamide 2,4-Diamino-6-phenyl-s-triazine 6-Phenyl-1,3,5-triazine-2,4-diamine Quantril Empirical C5H9N5 Formula C6HsC3N3(NH2)2... 

Anthracenedione, 1,1 -((6-phenyl-1,3,5-triazine-2,4-diyl) diimino) bis. See 1,1 -[(6-Phenyl-1,3,5-triazine-2,4-diyl) diimino] bis-9,10-anthracenedione... 

Phenyl tolyl ketone. See 2-M ethyl benzophenone Phenyl p-tolyl ketone. See 4-Methylbenzophenone Phenyl-o-tolyl-methanone. See 2-Methylbenzophenone 6-Phenyl-1,3,5-triazine-2,4-diamine. See Benzoguanamine... 

Phenyl-1,3,5-triazine-2,4-diyl) diimino] bis-9,10-anthracenedione 4125-43-3 o-Allyloxyanisole... 

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