An efficient synthesis of pyrrolo[2,3-d]pyrimidines via inverse electron demand diels-alder reactions of 2-amino-4-cyanopyrroles with 1,3,5-triazines.
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.
Dang
Qun
Q
Department of Medicinal Chemistry, Metabasis Therapeutics, Inc., 9390 Towne Centre Drive, Suite 300, San Diego, California 92121, USA. dang@mbasis.com
Gomez-Galeno
Jorge E
JE