2-Hydroxy-4,6-dimethoxy-1,3,5-triazine

As can be seen, the pathway from the cyclohexadienone to the ortho-rearranged phenol does not imply a jump over an energy barrier (34 kcal/mol), but a tunneling from the vibrational energy levels located at E(vo) = 0 kcal/mol and E(vi) = 3.9 kcal/mol (4.4 kcal/mol for the deuterated compound). Analogous results have been reported for the photo-Fries rearrangement of 2,4-dimethoxy-6-( ara-tolyloxy)-v-triazine (28) to give 2,4-dimethoxy-6-(2-hydroxy-5-meth-ylphenyl)-v-triazine (29) (Scheme 11) [43]. 

Methyl-3-[N-(l-phenyl-ethyl)-hydroxyamino]- -methylester E16a, 127 (R-NH-OH + En) Pyridin 3-(Dimethoxy-methyl)-4-(fnmy-3-hydroxy-cyclopentyl)-E7b/2, 483 C-[CH(OR)2]-1,2,4-triazin + 3-OH —1-(CO — CH3) — cyclopentan Pyridin-l-oxid 4-Ethoxy-2-(l-hydroxy-cyclohexyl)- E19d. 605 (H - Li/ -(- Keton) Pymolo l,2-a azepin 6-Ethenyl-5-methoxycarbonyl-3-oxo-(5R, 6S, 9aR )-octa-hy dro-E21b, 1974 l-[CH(OH) —... 

Dimetlioxy-2-(2-ainino-phenoxy)-triazin unterliegt bei Bestrahlung (X = 254 nm) einer Smiles-Umlagerung zu 6-(2-Hydroxy-anilino)-2,4-dimethoxy-l,3,5-triazin3 ... 

In all these methodologies, the co-product along with the formation of the desired product is 2-hydroxy-4,6-dimethoxy[l,3,5]triazine 136 (HO-DMT). This product can be recycled by treatment with POCI3 to give CDMT, which is further converted to DMTMM (Scheme 68) <2002TL3323>. 

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