Synthesis of 5-Hydroxythieno[2,3-d]pyrimidin-6(5H)-one Derivatives by the Reaction of 2-(4-Chloropyrimidin-5-yl)-2-hydroxyalkanoate with Sodium Hydrogensulfide

Kobayashi, Kazuhiro; Murayama, Ikuma; Ono, Ryoga; Fujiwara, Daiki; Hiyoshi, Hidetaka; Umezu, Kazuto

doi:10.3987/com-18-13911

Cited by 3 publications

(1 citation statement)

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“…Thieno[2,3-d]pyrimidines are purine bioisosteres coming to the center of interest due to their high structural diversity and well-documented spectrum of biological activity (for reviews, see refs − ). Much less is known on the preparation and reactions of partially saturated thieno[2,3-d]pyrimidines. − To study the reactivity of the prepared ADHTs 6 under Mannich conditions, their behavior upon treatment with a series of primary amines and HCHO was examined here.…”

Section: Resultsmentioning

confidence: 99%

2-Amino-4,5-dihydrothiophene-3-carbonitriles: A New Synthesis, Quantum Chemical Studies, and Mannich-Type Reactions Leading to New Hexahydrothieno[2,3-d]pyrimidines

et al. 2021

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trans-2-Amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles were prepared either by the reaction of 3-aryl-2-cyanothioacrylamides with α-thiocyanatoacetophenone or by the Michael-type addition of cyanothioacetamide to α-bromochalcones followed by intramolecular cyclization. The mechanism of the first reaction was studied using high-level quantum chemical calculations. Density functional theory (DFT) studies were carried out to determine the mechanism of the first reaction. A new approach toward the construction of the thieno[2,3-d]pyrimidine core system was demonstrated by the reaction of the prepared dihydrothiophenes with HCHO and RNH2 under noncatalyzed Mannich conditions.

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