An Efficient Synthesis of Pyrrolo[2,3-<i>d</i>]pyrimidines via Inverse Electron Demand Diels−Alder Reactions of 2-Amino-4-cyanopyrroles with 1,3,5-Triazines

Abstract

The scope of the inverse electron demand Diels-Alder reaction of 2-amino-4-cyanopyrroles (3a-e) with 1,3,5-triazines (1, 2) is reported. This methodology is suitable for one-pot syntheses of highly substituted and highly functionalized pyrrolo[2,3-d]pyrimidines that are the central heterocyclic nucleus of various nucleoside natural products such as toyocamycin, sangivamycin, and tubercidin.