One‐pot synthesis of novel substituted pyrrolo[2,3‐d]pyrimidines using dry media

Abstract

A convenient solvent‐free one‐pot synthesis of 1,3,5,7‐tetraaryl‐1,3,4,7‐tetrahydro‐2‐thio‐xopyrrolo[2,3‐d]pyrimidin‐4‐one derivatives using supported reagents under microwave irradiation is described. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:617–621, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20355

More Sustainable Approaches for the Synthesis of N-Based Heterocycles

“…Two other methods developed for the preparation of pyrroles and fused pyrroles in solvent-free conditions consist of two distinct couplings under MWI in a domestic microwave oven. The first method is based on the coupling of an α,β-unsaturated aldehyde or ketone, an amine, and a nitroalkane on the surface of silica gel (Scheme ), which was recently modified through introduction of N , N -disubstituted thiobarbituric acids instead of α,β-unsaturated aldehyde, to afford pyrrolo[2,3- d ]pyrimidines . The second method is a coupling of a carbonyl compound, an amine, and an α,β-unsaturated nitroalkene on the surface of alumina (Scheme ).…”

“…The first method is based on the coupling of an R,β-unsaturated aldehyde or ketone, an amine, and a nitroalkane on the surface of silica gel (Scheme 18), 145 which was recently modified through introduction of N,N-disubstituted thiobarbituric acids instead of R,β-unsaturated aldehyde, to afford pyrrolo [2,3-d]pyrimidines. 146 The second method is a coupling of a carbonyl compound, an amine, and an R,βunsaturated nitroalkene on the surface of alumina (Scheme 19). In this last procedure, the nitroalkene R-substituent (R 3 ) seems to be essential since its absence takes the reaction along different pathways.…”