1. Stable hemiaminals from axially chiral pyridine compounds
- Author
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Senel Teke Tuncel, Ilke Demir, Safiye Sağ Erdem, Ilknur Dogan, and Tuncel S. T., Demir I., ERDEM S., Dogan I.
- Subjects
Temel Bilimler (SCI) ,Mühendislik ,ENGINEERING ,stable hemiami ,Sağlık Bilimleri ,Biochemistry ,Physical Chemistry ,Organik Kimya ,Kimya ,Analytical Chemistry ,CHEMISTRY ,Biyokimya ,BİYOKİMYA VE MOLEKÜLER BİYOLOJİ ,Drug Discovery ,Kimya Mühendisliği ve Teknolojisi ,FARMAKOLOJİ VE ECZACILIK ,MÜHENDİSLİK, KİMYASAL ,PHARMACOLOGY & PHARMACY ,Spectroscopy ,PHARMACOLOGY & TOXICOLOGY ,İlaç Keşfi ,intramolecular hydrogen bonding ,Temel Bilimler ,Basic Pharmaceutics Sciences ,Spektroskopi ,Fizikokimya ,Life Sciences ,CHEMISTRY, ORGANIC ,Kataliz ,KİMYA, ANALİTİK ,MOLECULAR BIOLOGY & GENETICS ,Farmakoloji ve Toksikoloji ,Natural Sciences (SCI) ,Physical Sciences ,pyridine compounds ,Engineering and Technology ,Natural Sciences ,BIOCHEMISTRY & MOLECULAR BIOLOGY ,Sitogenetik ,2-iminothiazolidin-4-ol ,axially chiral hemiaminal ,Farmakoloji ,Life Sciences (LIFE) ,Molecular Biology and Genetics ,Chemical Engineering and Technology ,Catalysis ,CHEMISTRY, ANALYTICAL ,SPEKTROSKOPİ ,KİMYA, ORGANİK ,Yaşam Bilimleri ,Health Sciences ,Biyoinorganik Kimya ,Cytogenetic ,Engineering, Computing & Technology (ENG) ,Eczacılık ,Bioinorganic Chemistry ,Moleküler Biyoloji ve Genetik ,stable hemiaminal ,Pharmacology ,Organic Chemistry ,Mühendislik, Bilişim ve Teknoloji (ENG) ,Pharmacology and Therapeutics ,Temel Eczacılık Bilimleri ,Fizik Bilimleri ,Yaşam Bilimleri (LIFE) ,Analitik Kimya ,Mühendislik ve Teknoloji ,ENGINEERING, CHEMICAL - Abstract
© 2023 Wiley Periodicals LLC.In this study, we have synthesized a series of 3-(pyridin-2-yl)-2-(pyridin-2-ylimino)thiazolidin-4-ol derivatives regioselectively from 2-iminothiazolidin-4-ones using LiAlH4 at room temperature. Due to the presence of the restricted rotation around the N3-Caryl single bond, the formation of M/P isomers was observed. The OH group of the hemiaminal was found to orient itself on the same side with pyridyl nitrogen during this restricted rotation to form an intramolecular hydrogen bond, which was demonstrated by the computational DFT study. This orientation presumably inhibited the occurrence of dehydration and stabilized the molecule.
- Published
- 2023
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