By Henk C. van der Plas, Alan R. Katritzky
Degenerate ring modifications of heterocycles are categorised as reactions within which a heterocyclic approach is switched over into an analogous hetercyclic approach. This monograph covers an authoritative, finished assessment of a bunch of degenerate ring adjustments in 5- and 6-membered heterocycles. It indicates how by means of 15N-labeled, 13C-labeled or selectively substituted compounds those degenerate ring trnasformations will be found and hwo many of the effects could be defined by way of the Addition Nucleophile, Ring starting, Ring Closure [ANRORC] mechanism. one other major topci of the monograph is the occurance of degenerate ring modifications.
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Additional info for Advances in Heterocyclic Chemistry, Vol. 74
26, the reaction follows the same pattern of ring opening, 4-amino-1-cyano-4phenyl-1-aza-1,3-butadiene (45) is formed as intermediate, which by loss of double 15N-labeled carbodiimide (aminocyanogen) is transformed into unlabeled 4-amino-4-phenyl-1-aza-1,3-butadiene (46). The aminoacrylonitrile 40 is formed from 46 by a Cannizzaro-type oxidation–reduction reaction. 26 is that, in principle, from the intermediary 45 by ring closure a double 15 N-labeled 2-aminopyrimidine 42 can also be obtained!
Formation of 60 and 61, proving that under these reaction conditions the SN(ANRORC) mechanism plays only a very minor role in the amination. The strikingly different results obtained in the aminodehydrogenation at low temperature in liquid ammonia and those obtained at the high temperature in boiling xylene can be rationalized as follows. In liquid ammonia the C-2 and C-6 adducts are stabilized by solvation and therefore have a longer lifetime which allows isomerization. In the apolar solvent xylene, stabilization is very weak; therefore, they react SN(ANRORC) REACTIONS IN AZINES 51 immediately into their respective products.
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. This has indeed been experimentally established (see Section II,C,1,g). e. Aminodebromination of 5-Bromopyrimidines In Section II,A.