Short synthesis of polyfunctional sp3-rich threonine-derived morpholine scaffolds?
Organic & Biomolecular Chemistry Pub Date: 2017-11-06 DOI: 10.1039/C7OB02454A
Abstract
A convenient synthesis of novel complex morpholines was achieved by a two-step process involving a Petasis three-component coupling reaction of glycolaldehyde, organoboronic acid and different amines, followed by an acid- or base-mediated intramolecular cyclization. The use of threonine derivatives with glycolaldehyde in the Petasis reaction has been studied and successfully applied in the process, achieving morpholines with a higher fraction of sp3 carbon atoms compared to blockbuster drugs.
Recommended Literature
- [1] Alumina coating on 5 V lithium cobalt fluorophosphate cathode material for lithium secondary batteries – synthesis and electrochemical properties? S. Amaresh,K. Karthikeyan,K. J. Kim,Y. S. LeeRSC Adv., 2014,4, 23107-23115 10.1039/C4RA02318H
- [2] An insight into the hybridization mechanism of hairpin DNA physically immobilized on chemically modified graphenes Adeline Huiling Loo,Alessandra Bonanni,Martin PumeraAnalyst, 2013,138, 467-471 10.1039/C2AN36199J
- [3] Aggregation-induced emission enhancement in halochalcones? Patricia A. A. M. Vaz,Jo?o Rocha,Artur M. S. SilvaNew J. Chem., 2016,40, 8198-8201 10.1039/C6NJ01387B
- [4] An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile? Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo NamDalton Trans., 2016,45, 376-383 10.1039/C5DT04292E
- [5] An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand? Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-KerlidouChem. Sci., 2018,9, 4152-4159 10.1039/C7SC04348A
- [6] An atomic scale study of defects in Co2FeAl Ravi Kumar Yadav,R. GovindarajPhys. Chem. Chem. Phys., 2020,22, 26876-26886 10.1039/D0CP04572A
- [7] An apparatus for determining small amounts of alchohol in sour milk and urine Analyst, 1964,89, 272-275 10.1039/AN9648900272
- [8] An artificial CO-releasing metalloprotein built by histidine-selective metallation? Inês S. Albuquerque,Hélia F. Jeremias,Miguel Chaves-Ferreira,Dijana Matak-Vinkovic,Omar Boutureira,Carlos C. Rom?oChem. Commun., 2015,51, 3993-3996 10.1039/C4CC10204E
- [9] An intermolecular C–H oxidizing strategy to access highly fused carbazole skeletons from simple naphthylamines? Christian K. Rank,Alexander W. Jones,Tatjana Wall,Patrick Di Martino-Fumo,Sarah Schr?ck,Markus Gerhards,Frederic W. PatureauChem. Commun., 2019,55, 13749-13752 10.1039/C9CC05240B
- [10] An automatic determination of thoria in thoria-urania mixtures Analyst, 1966,91, 208-210 10.1039/AN9669100208
Journal Name：Organic & Biomolecular Chemistry
research_products
-
CAS no.: 89640-58-4
![N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide](https://ossimg.kuujia.com/scimg/1444500/1444113-98-7x500.png)
![1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol](https://ossimg.kuujia.com/scimg/1271000/1270529-38-8x500.png)
![2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid](https://ossimg.kuujia.com/scimg/2138500/2138166-62-6x500.png)
![2-(1H-indol-3-yl)-N-{[6-(thiophen-2-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl}acetamide](https://ossimg.kuujia.com/scimg/2034500/2034271-14-0x500.png)