Download Advances in Heterocyclic Chemistry, Vol. 74 by Henk C. van der Plas, Alan R. Katritzky PDF

By Henk C. van der Plas, Alan R. Katritzky

Degenerate ring variations of heterocycles are categorised as reactions within which a heterocyclic method is switched over into a similar hetercyclic process. This monograph covers an authoritative, finished assessment of a bunch of degenerate ring alterations in 5- and 6-membered heterocycles. It exhibits how by way of 15N-labeled, 13C-labeled or selectively substituted compounds those degenerate ring trnasformations will be came upon and hwo lots of the effects might be defined by way of the Addition Nucleophile, Ring establishing, Ring Closure [ANRORC] mechanism. one other major topci of the monograph is the occurance of degenerate ring changes.

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Extra info for Advances in Heterocyclic Chemistry, Vol. 74

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34). Amination of 5-phenylpyrimidine with 15N-labeled potassium amide revealed that no label was incorporated in the pyrimidine ring of 6-amino-5phenylpyrimidine; this means that exclusively 72 has been formed. However, in 2-amino-5-phenylpyrimidine, the pyrimidine ring did contain the 15N label. From the mass spectral data it was calculated that the ratio 70 : 73 is about 20 : 80, proving that about 80% of 5-phenylpyrimidine participates in the SN(ANRORC) mechanism. 34). 4-t-Butylpyrimidine. Reaction of 4-t-butylpyrimidine with potassium amide/liquid ammonia provided a mixture of both 2-amino-4-t-butyl(25%) and 6-amino-4-t-butylpyrimidine (40%) (82RTC367).

For example, the amination of 2-chloro-4-phenylpyrimidine, when carried out at Ϫ33°C instead of Ϫ75°C, still occurs 90% according to the ANRORC mechanism. 24). Treatment of an independently prepared specimen of 2-amino-4-phenyl [1,3-15N]pyrimidine with potassium amide/liquid ammonia under varying reaction conditions gave no indication of a rearrangement leading to 15N enrichment in the exocyclic amino group. 25). In this way the reaction occurs analogously as discussed with the 6-halogeno-4-phenylpyrimidines.

This is based on the observation that in the retrieved starting material no decrease of the 15N content was observed. If cyclization would have taken place before loss of the hydrogen bromide, then the 1 : 1 C-6 amino adduct 55 would have been formed, which is in equilibrium with the starting material, and a decrease of the 15N content in the retrieved starting material should have been found. As indicated previously, this is not observed. 28). 7) (78JHC1121). As mentioned previously, only in the amination reaction of 4-piperidino5-bromopyrimidine was an SNH tele amination observed.

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