Synthesis and DFT analysis of non-covalent interactions in crystal structures of 6-R-2-alkoxy-, 2,3-di-, and 2,2,3-tri-tert-butylpyrrolo[1,2-b][1,2,4]triazines.

ABSTRACT: Novel 7-amino-3-tert-butyl-2-OR¹-6-R²-pyrrolo[1,2-b][1,2,4]triazine-8-carbonitriles (R¹ = CH₂CO₂Et, CH₂Boc, Me, n-Bu; R² = CO₂Et, CO₂ n-Bu, CO₂ t-Bu, C₆H₄CO₂ i-Pr) have been synthesized and investigated by X-ray diffraction. Nucleophilic replacement of an alkoxy group with t-BuLi afforded sterically hindered tert-butyl 7-amino-2,3-di-tert-butyl- and 2,2,3-tri-tert-butyl-8-cyanopyrrolo[1,2-b][1,2,4]triazine-6-carboxylates. The lengths and bond angles as well as packing modes of molecules in crystals have been considered. The non-covalent interactions such as the changes in the H-bonding and close contacts were analyzed by DFT and the Hirshfeld surfaces and compared for different substituents.

Supplementary information

The online version contains supplementary material available at 10.1007/s11224-022-02006-x.

SUBMITTER: Koltun DS 

PROVIDER: S-EPMC9296897 | biostudies-literature | 2023

REPOSITORIES: biostudies-literature