Crystalline State Hydrogen Bonding of 2-(2-Hydroxybenzylidene)Thiazolo[3,2-<i>a</i>]Pyrimidines: A Way to Non-Centrosymmetric Crystals

Abstract

Thiazolopyrimidines are attractive to medical chemists as new antitumor agents due to their high inhibiting activity towards the tumor cells replication process and easy modification of their structure by varying of the number and nature of substituents. The presence of asymmetric C5 carbon atoms requires the development of racemic mixture separation procedures for these heterocycles. One of the more effective ways is the crystallization of a racemic compound as a conglomerate. A prerequisite for such separation is the formation of non-centrosymmetric crystals presenting Sohncke space groups. For the construction of chiral supramolecular ensembles in a crystalline state, hydrogen bonds were chosen as supramolecular synthons. In this context, salicylic derivatives at the C2 atom of thiazolopyrimidines were synthesized. The crystal structures of the obtained compounds were established by SCXRD. The regularities of the solvent’s influence on the crystal packaging were revealed. The conditions for the preparation of crystals with the chiral space group due to intermolecular hydrogen bonds were discovered.

Keywords

• thiazolo[3,2-<i>a</i>]pyrimidines
• solid state structure
• hydrogen bonds
• non-centrosymmetric crystals