By Henk C. van der Plas, Alan R. Katritzky
Degenerate ring changes of heterocycles are categorised as reactions during which a heterocyclic process is switched over into an analogous hetercyclic method. This monograph covers an authoritative, accomplished assessment of a bunch of degenerate ring ameliorations in 5- and 6-membered heterocycles. It exhibits how by way of 15N-labeled, 13C-labeled or selectively substituted compounds those degenerate ring trnasformations could be found and hwo many of the effects may be defined by means of the Addition Nucleophile, Ring beginning, Ring Closure [ANRORC] mechanism. one other major topci of the monograph is the occurance of degenerate ring alterations.
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Additional resources for Advances in Heterocyclic Chemistry, Vol. 74
It can be argued that in this anion most of the negative charge is localized in the N-1, C-2, N-3 region, making the nucleophilic attack at position 2 less favorable than addition at C-6, because of electron repulsion between the incoming amide ion and the highly charged region around position 2. 30. f. Aminodemethoxylation of Dimethoxypyrimidines It has been reported that 4,6-dimethoxypyrimidine and its 5-bromo derivative undergo an aminodemethoxylation to the corresponding 4-methoxy-6-aminopyrimidines on treatment with potassium amide/liquid ammonia (61JCS1298; 65JCS6659).
Hydrochloric acid. The 15N content in both the 6-amino and the 6-chloro compound is the same, providing clear evidence that in the amino demethoxylation under described conditions the SN(ANRORC) mechanism is the sole operative process. 31). 31) (70RTC680). One of the intermediates is 3-cyanomethyl-1,2,4-triazole, which in the presence of hydrazine is decyanated. 31 g. Aminodehydrogenation of Pyrimidines The conversion of pyridine into 2-aminopyridine (known as the Chichibabin amination) was considered for a long time to be a typical and outstanding example of an aminodehydrogenation reaction (14MI1; 71MI2; 78RCR1042) and received scant recognition as a method for aminating pyridines and related azines.
It was stated that the slowly occurring amination of 5bromo-4-t-butyl-6-deuteriopyrimidine in liquid ammonia (24 hr, 2 equiv. of potassium amide) gives in about 30% yield the cine-substituted product 6amino-4-t-butylpyrimidine, in which no deuterium was present (64TL2093; 65TL555; 68TL9). This result was interpretated as a strong indication for the intermediacy of 4-t-butyl-5,6-pyrimidyne (5,6-didehydropyrimidine), which undergoes a one-sided addition at C-6. However, for proton abstraction at C-6, the initial step in the 5,6-pyrimidyne formation, no evidence was found.
Advances in Heterocyclic Chemistry, Vol. 74 by Henk C. van der Plas, Alan R. Katritzky