Rings Ritter reaction

In this modified Ritter reaction inversion at C-3 takes place, implying that the five-membered rings 40 have a czs-relationship between the alkyl substituent... 

Epoxides also participate in the Ritter reaction with nitriles. An investigation of the ring opening of several alkyl-substituted glycidic esters and amides 181 showed that this transformation occurs with inversion and is completely regiospecific. ° Esters appeared to be somewhat more reactive than amides. However, phenyl-substituted glycidic esters and amides 184 are almost totally nonstereoselective. In addition, the oxazolines 186 are isolated in low yield due to the propensity of intermediate 185 to generate an aldehyde byproduct 187 (Scheme 8.53). 

The first synthesis of a heterocyclic system (22) by the Ritter reaction was reported24 in 1952, from the reaction of nitriles with methyleugenol (19). The reactions succeed only when the benzene ring is activated and allylbenzene itself gives the expected amide. 

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