One‐pot, Three‐component Synthesis of a Series of New Bis‐pyrrolo[2,3‐d]pyrimidines in the Presence of TPAB under Reflux Conditions

Abstract

A one‐pot, three‐component reaction of 1,4‐phenylene‐bis‐glyoxal, 6‐aminouracils, and dimedone or barbituric acid derivatives in the presence of tetrapropylammonium bromide (5 mol%) in ethanol under reflux conditions gave a series of new bis‐pyrrolo[2,3‐d]pyrimidine derivatives in high yields.

Aminouracil and aminothiouracil as versatile precursors for a variety of heterocyclic systems

“…79 Scheme 16. Synthesis of pyrrolo [2,3-d]pyrimidine derivatives 39a-g. Sabegh et al 80 reported the synthesis of bis-pyrrolo [2,3-d]pyrimidine derivatives 41a-g and 43a-e through a multicomponent reaction of 1,4-phenylene-bis-glyoxal (40) with 6-aminouracil derivatives 3 or 6 and either barbituric acid 37 or dimedone (42) (Scheme 17, Table 6). Thiazolo[3,2-a]pyrimidin-5-ones 51a-f were obtained in good yields via reaction of the appropriately substituted phenacyl halides 50 with 6-substituted anilino-2-thiouracil 49 (prepared from the reaction of 6amino-2-thiouracil (6) with substituted anilines 47 in the presence of aniline hydrochloride 48 at high temperature) in the presence of anhydrous potassium carbonate followed by cyclization upon heating with conc.…”