Abstract
Our work exploring the synthesis and optimization of increasingly hindered thiols led to the synthesis and crystal structure determination of the title compound, C5H8N2OS, a dimethly-substituted 4-thiazolidinone. The molecular packing exhibits a herringbone pattern with the zigzag running along the b-axis direction; the compound crystallizes as chains of hydrogen-bonded dimers formed by N—H...N hydrogen bonds, which build centrosymmetric R 2 2(8) ring motifs in the crystal.
Highlights
As a result of their impressive array of biological responses and potential uses in medicine, 4-thiazolidinones and their derivatives have been extensively investigated in recent years
The title compound provides an avenue for a new substitution pattern that is not often seen in the literature, namely, a geminal dialkyl substitution at the 5-position on the ring
This motif may provide a unique utility since a more thermodynamically favored confirmation may result because of steric hindrance, especially if the thiazolidinone is further substituted at the 2- and/or N-positions (Vigorita et al 1979)
Summary
As a result of their impressive array of biological responses and potential uses in medicine, 4-thiazolidinones and their derivatives have been extensively investigated in recent years Their wide range of biological relevance includes anticancer, antiviral, antibacterial (Tripathi et al, 2014), analgesic (Kumar & Patil, 2017) and antipsychotic (Kaur et al, 2010) properties. The title compound provides an avenue for a new substitution pattern that is not often seen in the literature, namely, a geminal dialkyl substitution at the 5-position on the ring This motif may provide a unique utility since a more thermodynamically favored confirmation may result because of steric hindrance, especially if the thiazolidinone is further substituted at the 2- and/or N-positions (Vigorita et al 1979).
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