Non‐Aromatic 3H‐Pyrroles in the Reaction with Nucleophiles: Is High Reactivity a Myth?

Abstract

The reactivity of azadiene system of non‐aromatic 3H‐pyrroles toward nitrogen‐, oxygen‐, and sulfur‐nucleophiles has been evaluated both experimentally and theoretically. The obtained results demonstrate, for the first time, low reactivity of 3H‐pyrrole system and allow future research directions in the chemistry of this unique heterocyclic scaffold to be formulated.

Synthesis of Pyrrolo[2,1-a]isoquinolinium Salts from 1-Pyrrolines and Alkynes via Rhodium-Catalyzed C–H Functionalization/N-Annulation Tandem Reaction

“…Pentamethyl­cyclo­pentadienyl rhodium dichloride dimer [Cp*RhCl 2 ] 2 was prepared following the published procedure . Starting pyrrolines, , prop-1-yn-1-ylbenzene, methyl 3-phenylpropiolate and other alkynes were synthesized according to the literature methods. The detailed procedures for the synthesis of 5-butoxypyrroline 1a - d 5 and 1,2-bis­(4-nitrophenyl)­ethyne 2e are given in the Supporting Information.…”