80947-49-5

Upstream product

• 4270-27-3 6-chlorouracil 
• 106-45-6 para-thiocresol 

Downstream Products

• 80947-59-7 2,4-Dioxo-6-p-tolylsulfanyl-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 

Relevant academic research and scientific papers

Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study

In this study, three new 6-(arylthio)uracil derivatives, namely, 6-(phenylthio)pyrimidine-2,4(1H,3H)-dione (1), C10H8N2O2S; 6-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione (2), C11H10N2O2S; and 6-(3,5-dimethylphenylthio)pyrimidine-2,4(1H,3H)-dione (3), C12H12N2O2S, have been synthesized. Single-crystal structures of these compounds reveal an invariant molecular tape contains alternate R22(8) synthons formed by N-H···O hydrogen bonds in 1 and 3. This alternate hydrogen-bonded pattern disappeared in 2; instead, a new synthon is generated. The lattice energy calculation suggests that the methyl-substituted derivatives (2 and 3) have high stabilization energy than compound 1. The electrostatic potential map reveals the difference in the accepting tendency of the carbonyl oxygen. The Hirshfeld surface and 2D-fingerprint plots analyses demonstrate that the major intermolecular interactions come from H···O contacts in 1, and these contacts were reduced due to the presence of methyl substitutions in 2 and 3. This reduction is compensated by the increase of the same amount of H···H contacts in these structures. Further, the PIXEL energy and DFT calculations at the M06-2X-D3/cc-pVTZ level of theory were used to characterize the dimeric topology formed in structures of 1-3. The intermolecular interaction energies of dimers calculated by the PIXEL method were compared with the B97D3/def2-TZVP level of approximation. Although these molecules' crystal packing is somewhat different, the energy frameworks show similarities on the respective crystal structure's shortest axis. Furthermore, the nature and strength of various noncovalent interactions such as N-H···O, C-H···O/S/π, π···π, and a chalcogen bond of type C-S···O═C were evaluated using the Bader's quantum theory of atoms-in-molecules framework.

Synthesis and Properties of 1-Benzothiopyranopyrimidine-2,4-(3H)diones (10-Thia-5-deazaflavins)

Treatment of 6-arylthiouracils with the Vilsmeier reagent (dimethylformamide-phosphorus oxychloride) gave the corresponding 6-arylthio-5-formyluracils, which could alternatively be prepared by the condensation of 6-chloro-5-formyluracils with thiophenols.Dehydrative cyclization of the above 5-formyluracils with polyphosphoric acid gave 1-benzothiopyranopyrimidine-2,4-(3H)diones (10-thia-5-deazaflavins).These 10-thia-5-deazaflavins oxidized alcohols to give the corresponding carbonyl compounds with the aid of strong base, and they were hydrogenated to 1,5-dihydro-10-thia-5-deazaflavins.Treatment of 10-thia-5-deazaflavins with the concentrated aqueous potassium hydroxide led to the exclusive formation of 1,5-dihydro-10-thia-5-deazaflavins and 1,5-dihydro-10-thia-5-deazaflavins-5-ones via intermolecular oxidation-reduction (disproportionation) between initially formed 1,5-dihydro-5-hydroxy-10-thia-5-deazaflavins and unchanged 10-thia-5-deazaflavins.