2- -l-anilino

Diaminopyrimidines (22) were also cyclized with cyanogen bromide (90JHC851) or phenyl isothiocyanate (97PHA753) to give the corresponding 2-amino- or 2-anilino-l,2,4-triazolo[l,5-c]pyrimidines 30 and 31 respectively (Scheme 15). 

The reaction of 2-anilino-l,4-naphthoquinone 374 with benzoylacetic acid hydrazide gives 3-hydrazino-pyrazolyl derivative 375, that is acetylated to produce 5-[[l,4-dihydro-l,4-dioxo-3-(phenylamino)-2-naphthalenyl]sulfonyl]-3-methyl-6-phenyl-5/7-pyrazolo[5,l-c][l,2,4]triazole 51. This latter derivative is also obtained in 51% yield from reaction of 374 with benzoylacetic acid hydrazide in the presence of a mixture of acetic acid-sodium acetate <2004PS(179)1907> (Scheme 39). 

Hg(0-C0-CH3)2 h5c6—nh2 20-25° 3h 20-25° 15 min 2-Anilino-l-( diethyl-methyl-sUylj-ethan 65 3... 

H3C6-NH2/l,4-Dioxan, 90% 1-3 h dann isolieren 2. N2H4 H20/Raney-Ni/H3C-0H 20 25% 1 h NH—C6H5 NH2 [2-Anilino-l-phthalimidoamino-cyclohexan - ] trans-2-Amino-1-anilino-cydo-hexan [78] 83 1... 

D° [Amin Oxiran 1 1] Zeolith ZCP-50/ Benzol, Ruckfl. 9 h [Amin Oxiran — 1 1] Zn-(2 J ,3 R)-tartrat/ CH2C12, 20-25% 7d 1 Anilino-2-hydroxy-octan + 2-Anilino-l-hydroxy-octan (-7 3) (1 R,2R)-2-Anilino-l-hydroxy-cyclohexan (ee 52 %) 90 28 3 4... 

The unsubstituted 1,3,4-thiadiazole is sufficiently basic to give a stable hydrochloride and hydrobromide, but it is described as very weakly basic, though no pK value has been published. 2-Amino- and 2-anilino-l,3,4-thiadiazoles are also weak bases, whereas the tautomeric imines are somewhat stronger. pK values have been useful in tautomerism studies, and some pKg values, i.e., pK values of the conjugate acids, have been collected in Table II and will be discussed in the following section. 

Amino-1-brom-1 -phenyl- ( —HC1) E16d, 1196 (En + -NBr2) 2-Anilino-l-brom- V/4, 376 Pyridin 2-Brom-4-propyl- V/4, 450... 

Ar — CH = N — OH + R2B-CH2-CH = CH-CH3) Cyclopentan 2-Anilino-l-hydroxy-E16d, 1124 (Addition/Hydro-lyse)... 

Cyclohexan 2-Anilino-l-chlor- E2ie, 5426 (En + Ar N3/AlCl3) Propanimin 2-Chor-N-isopropyl-2-phenyl- E14b, 242 (R-CHO + Amin)... 

Anilino-l-hydroxy- E16d, 1125/ 1209 (Oxiran + Amin) 2-Hydroxy-l-[(2-... 

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