Open AccessSynthesis of Pyrrolopyrazinones by Construction of the Pyrrole Ring onto an Intact Diketopiperazine
Author(s) -
Susanna K. Maisto,
Angela P. Leersnyder,
Gwyneth L. Pudner,
Jonathan R. Scheerer
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01263
Subject(s) - chemistry , pyrrole , annulation , aldol reaction , bicyclic molecule , aldol condensation , alkyne , lewis acids and bases , ring (chemistry) , lewis acid catalysis , stereochemistry , catalysis , combinatorial chemistry , organic chemistry
This study reveals an alternative sequence for the synthesis of compounds that contain the pyrrolodiketopiperazine structural motif. Starting with a diketopiperazine precursor, a mild aldol condensation precedes pyrrole annulation and bicyclic ring fusion. The derived intermediate aldol condensation products, which bear either a protected carbonyl or a functionalized alkyne, can be cyclized to the pyrrolodiketopiperazine by protic or gold Lewis acid catalysis.