2-Substituted Hexahydropyrimidines and Their Tautomerism

Tautomeric equilibria analysis of β‐ketoamides by mass spectrometry

“…β‐Ketoamides are versatile intermediates for the synthesis of several heterocycles: 3‐acyltetramic acids (used in the total synthesis of tirandamycin and other related natural antibiotics), pyrans, alkaloids, lactams and spirolactams, azetidin‐2‐ones, as well as several 3‐hydroxyisothiazol bioisosteres of glutamic acid and analogs of the AMPA receptor agonist . Some β‐ketoamides have been converted into γ‐ketoamides, a class of compounds related with a wide variety of biologically relevant systems …”

Substituent, Temperature and Solvent Effects on the Keto-Enol EQUILIBRIUM in <i>β</i>-Ketoamides: A Nuclear Magnetic Resonance Study

“…The importance of studying β-ketoamides arises from their versatility as intermediates in the synthesis of several heterocycles: 3-acyltetramic acids [7] (used in the total synthesis of tirandamycin and other related natural antibiotics [8]), pyrans [9], alkaloids [10], lactams and spirolactams [11], azetidin-2-ones [12], as well as several 3-hydroxyisothiazol bioisosteres of glutamic acid and analogs of the AMPA receptor agonist [13]. Moreover, some β-ketoamides have been converted into γ-ketoamides, a class of compounds related with a wide variety of biologically relevant systems [14].…”

A comparison of the electron ionization and electrospray behaviour of some N,N′‐disubstituted hexahydropyrimidines

“…In organic synthesis, the hexahydropyrimidine nucleus has been employed as a protecting group in selective acylations and additions of 1,3‐diamines, due to its easy cleavage in mild acidic medium,11, 12 while some derivatives are synthetic intermediates for antineoplastic drugs and structural units in new trypanothione reductase inhibitors 13, 14. Some recent reports have been devoted to the study of ring‐chain tautomerism in hexahydropyrimidines,15–17 their benzo‐fused derivatives (1,2,3,4‐tetrahydroquinazolines),18 and related compounds 19–21…”