Use of 1,3-dioxin-4-ones and related compounds in synthesis. Part 37. 5-Trifluoromethyl-1,3-dioxin-4-ones as versatile building blocks for trifluoromethylated aliphatic compounds

Author(s):  
Tomoyasu Iwaoka ◽  
Tomoko Murohashi ◽  
Nobuya Katagiri ◽  
Masayuki Sato ◽  
Chikara Kaneko
2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Aleksey E. Kuznetsov

Abstract Various (metallo)porphyrins and related compounds have been intensively investigated by different research groups due to their extremely important role in living organisms along with their versatile applications in technology. The design of novel porphyrinoids by core-modification, or substitution of pyrrole nitrogens, with the elements of other groups of the Periodic Table has been considered as a highly promising methodology for tuning structures and properties of porphyrinoids and thus opening new possible applications for them. Much effort has been given to the modifications of the porphyrin core with elements of the main groups, namely O, S, Se (chalcogens), and the heavier congener of nitrogen, phosphorus. In general, the porphyrin core modification by replacing nitrogens with heteroatoms is a promising and effective strategy for obtaining new compounds with unusual structures and properties (optical, electrochemical, coordinating, etc.) as well as reactivity. These novel molecules can also be employed as promising building or construction blocks in various applications in the nanotechnology area.


Synlett ◽  
2021 ◽  
Author(s):  
Peter Langer

AbstractThe synthesis of 1,3-selenazoles and related compounds, including 2,4,5-trisubstituted, 2,4-disubstituted, 4,5-disubstituted, 4-substituted 1,3-selenazoles, and parent unsubstituted 1,3-selenazole, is highlighted. Emphasis is also given on 2-benzoyl-1,3-selenazoles which can be functionalized by Knoevenagel reactions or by rearrangements via their corresponding oximes. Syntheses of bis-, tris-, and tetrakis(1,3-selenazoles) are discussed as well. 1,3,4-6H-Selenadiazines are available from selenosemicarbazides and can undergo ring-contraction or deselenation reactions. Most syntheses rely on the application of selenocarboxylic amides, selenourea and related building blocks which are conveniently available by reaction of the corresponding oxygen analogues with P4Se10.1 Introduction2 Selenocarboxylic Amides3 2,4,5-Tri- and 2,4-Disubstituted 1,3-Selenazoles4 Bis(1,3-selenazoles)5 2-Amino-1,3-selenazoles6 2-Unsubstituted 1,3-Selenazoles7 1,3,4-Selenadiazines8 Conclusions


2014 ◽  
Vol 3 (5) ◽  
pp. 311-314 ◽  
Author(s):  
R. F. M. Frade ◽  
J. A. S. Coelho ◽  
S. P. Simeonov ◽  
C. A. M. Afonso

Toxicity of hydroxymethylfurfural and 21 derivatives was assessed. Important guidelines for selection of more human friendly building blocks were obtained.


2008 ◽  
Vol 61 (7) ◽  
pp. 506 ◽  
Author(s):  
Magne O. Sydnes ◽  
Anna Bezos ◽  
Christopher Burns ◽  
Irma Kruszelnicki ◽  
Christopher R. Parish ◽  
...  

A series of enantiomerically pure C8c–C15 monoseco analogues, 23–30, of the alkaloids cryptopleurine (1) and julandine (2) have been prepared using cinnamyl chloride 37 and (S)- or (R)-2-methylpiperidine as key building blocks. Two related compounds, 31 and 32, have also been synthesized. Each of these analogues has been subjected to various biological evaluations and most of them show dramatically reduced cytotoxicity compared with parent system 1. Nevertheless, they are potent anti-angiogenic agents. The formation and single-crystal X-ray analysis of the spirocyclic dienone 54, a by-product arising from attempts to prepare analogue 32, is also described.


Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3369-3396 ◽  
Author(s):  
Jacek G. Sośnicki ◽  
Tomasz J. Idzik

2-Pyridone is characterized by a very wide range of reactivity of a different nature, ranging from electrophilic aromatic substitution, CH–metal-mediated reactions, and NH/OH functionalization of both possible lactam/lactim tautomers, through cycloaddition, to nucleophilic addition and transformation of the tautomeric C=O/C–OH moiety. The high availability of 2-pyridones and the possibility of their far-reaching functionalization additionally increased their values. Therefore, they are very useful building blocks for the synthesis of structurally diverse piperidine and pyridine compounds, including naturally occurring 2-pyridones. This review reports on the use of simple 2-pyridones in the synthesis of alkaloids and alkaloids-inspired compounds based on the piperidine or pyridine framework.1 Introduction2 Structure, Availability, and Reactivity of 2-Pyridones3 Monocyclic Piperidine Alkaloids from 2-Pyridones4 Polycyclic Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds from 2-Pyridones4.1 New Ring Formation Involving C/N Atoms of the 2-Pyridone Ring4.1.1 Indolizine-Fused 2-Pyridones: Camptothecins and Related Compounds4.1.2 Other Indolizines from 2-Pyridones4.1.3 Compounds Bearing the Quinolizine Ring System4.2 New Ring Formation Involving C/C Atoms of the 2-Pyridone Ring4.2.1 C-2/C-3 Ring Fusion4.2.2 C-3/C-4 Ring Fusion4.2.3 C-4/C-5 Ring Fusion4.2.4 C-5/C-6 Ring Fusion4.2.5 C-2/C-4 Ring Bridge4.2.6 C-2/C-6 Ring Bridge4.2.7 C-3/C-5 Ring Bridge4.2.8 C-3/C-6 Ring Bridge4.2.9 C-4/C-6 Ring Bridge5 Conclusion


1992 ◽  
Vol 47 (4) ◽  
pp. 547-552 ◽  
Author(s):  
Zeynel Kılıç ◽  
Edwin Weber ◽  
Necla Gündüz ◽  
Emine Kılıç ◽  
Hasan Nazır ◽  
...  

A number of macrocyclic (1b-3b) and linear oligoether compounds (4b-8b) with 2,2'- methylenebis(4-aminophenol) or 2-aminophenol characteristic building blocks have been synthesized by reduction of the corresponding nitro derivatives with Pd -C/hydrazine hydrate. The pKa' values of the new compounds have been determined by potentiometric titration. These and the observed spectroscopic data are discussed and compared with related compounds. A crystalline 1:1 complex of the diamino crown 3b with NaSCN has also been prepared and characterized.


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