Ueber die Einwirkung von Zimmtaldehyd auf Phenyltoluidoacetonitril

Synthesis of (–)‐(S)‐Norlaudanosine, (+)‐(R)‐O,O‐Dimethylcoclaurine, and (+)‐(R)‐Salsolidine by Alkylation of an α‐Aminonitrile

“…The resulting stabilized carbanions can be used as starting materials for the preparation of pyrrolidines, pyrroles, γ-amino acids, 1,2-diamines, or indoles in one-pot reaction procedures. [11][12][13][14][15][16] C-Alkylation of deprotonated unprotected aminonitriles 1 affords α-branched products 2, from which HCN can be eliminated to form ketimines 3. [17] Depending on the structure of the compound 3, this elimination may occur spontaneously.…”

Heterocycles from α‐Aminonitriles

“…[24] They observed the formation of pyrroles 3 from cinnamaldehyde (2) and a,Ndiarylaminonitriles 1 in methanolic KOH solution. [24] They observed the formation of pyrroles 3 from cinnamaldehyde (2) and a,Ndiarylaminonitriles 1 in methanolic KOH solution.…”

“…Von Miller and Plöchl reported as early as in 1898 that α‐aminonitriles are capable of 1,4‐additions to α,β‐unsaturated carbonyl compounds in a basic environment 24. They observed the formation of pyrroles 3 from cinnamaldehyde ( 2 ) and α, N ‐diarylaminonitriles 1 in methanolic KOH solution.…”

The Synthesis of the Pyrrole Ring

“…(138) The original structural assignments for the products led to the proposal of the reaction sequence (C17) + (C18)->(C19) ->(C20)->(C21), but subsequent determination of the orientation of the substituents showed the correct structure of the products to be (C24). (138) The original structural assignments for the products led to the proposal of the reaction sequence (C17) + (C18)->(C19) ->(C20)->(C21), but subsequent determination of the orientation of the substituents showed the correct structure of the products to be (C24).…”