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

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

ISBN-10: 0120207745

ISBN-13: 9780120207749

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

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Extra resources for Advances in Heterocyclic Chemistry, Vol. 74

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6 PERCENT YIELDS/100 [A] AND PERCENTAGE SN(ANRORC) MECHANISM/100 [B] OBTAINED IN THE AMINATION OF 2-X-4PHENYLPYRIMIDINES, XANRORC [A ϫ B], NONRESONANCE CONSTANTS F, AND RESONANCE FACTORS R OF SUBSTITUENTS X. 000 a The SO2CH3 group is deprotonated and the F and R values are unknown. 90. This equation gives a rather reliable and quantitative description of the influence on the amide-induced replacement of the leaving group in 2-X-4-phenylpyrimidines. 55 reflects the fraction of the molecules of 4-phenylpyrimidine (R and F are zero) that undergoes an SN(ANRORC) aminodehydrogenation.

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).

In the aminodechlorination of 4-piperidino-6-chloropyrimidine (potassium amide in liquid amonia, at Ϫ33ЊC), the SN(ANRORC) mechanism is only operative for 21%, whereas in the aminodechlorination of 4-anilino- and 4-methyl-6chloropyrimidine, no ring-opening is involved. It has been assumed that in this strong basic medium, the anilino group as well as the methyl group are deprotonated to form a charge-delocalized anion with an enhanced electron density at positions N-1 and N-3. In this anion the addition at C-2, the initial step in the ANRORC mechanism, is strongly disfavored, making the SN(ANRORC) process highly unlikely.

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


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