Adventures in 1,3-Selenazole Chemistry

Synlett ◽  
2021 ◽  
Author(s):  
Peter Langer
Keyword(s):  
Building Blocks ◽  
Ring Contraction ◽  
Related Compounds

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

Core-modified porphyrins: novel building blocks in chemistry

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Aleksey E. Kuznetsov
Keyword(s):  
Periodic Table ◽  
Building Blocks ◽  
Effective Strategy ◽  
Research Groups ◽  
Structures And Properties ◽  
Porphyrin Core ◽  
Living Organisms ◽  
New Compounds ◽  
Related Compounds ◽  
Nitrogen Phosphorus

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.

Heterocyclic compounds from alloxan and amines. XI. Uramils, dialuric acids, and related compounds

1970 ◽  
Vol 23 (6) ◽  
pp. 1229 ◽  
Author(s):  
JW Clark-Lewis ◽  
K Moody
Keyword(s):  
Acetic Acid ◽  
Anthranilic Acid ◽  
Heterocyclic Compounds ◽  
Aqueous Ethanol ◽  
Substituted Anilines ◽  
Pyrimidine Derivatives ◽  
Ring Contraction ◽  
Related Compounds

Preparation of a number of uramils and 5-aryldialuric acids from o-substituted anilines is described. Methylation of the uramils gave dimethoxy-N-monomethyl pyrimidine derivatives accompanied by minor amounts of trimethoxy-pyrimidines, and the dialuric acids gave 1,3-dimethylpyrimidines or 5-methoxy-1,3-dimethylbarbituric acids (with an excess of diazomethane). Ring contraction of the 1,3-dimethyldialuric acids gave the isomeric 5-N-methylcarbamoyloxazolidine-2,4-diones. The dialuric acid from dimedone gave a trimethyl derivative (a methoxycyclohexenyl-1,3-dimethyldialuric acid). Anthranilic acid and alloxan in acetic acid gave a benzoxazonespirobarbituric acid, but in aqueous ethanol yielded a dialuric acid which was characterized by conversion into several derivatives. Infrared and N.M.R. data are recorded for the uramils, dialuric acids, and their derivatives.

scholarly journals An emerging platform from renewable resources: selection guidelines for human exposure of furfural-related compounds

2014 ◽  
Vol 3 (5) ◽  
pp. 311-314 ◽  
Author(s):  
R. F. M. Frade ◽  
J. A. S. Coelho ◽  
S. P. Simeonov ◽  
C. A. M. Afonso
Keyword(s):  
Renewable Resources ◽  
Human Exposure ◽  
Building Blocks ◽  
Related Compounds ◽  
Selection Of

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

Synthesis and Biological Evaluation of Some Enantiomerically Pure C8c - C15 Monoseco Analogues of the Phenanthroquinolizidine-Type Alkaloids Cryptopleurine and Julandine

2008 ◽  
Vol 61 (7) ◽  
pp. 506 ◽  
Author(s):  
Magne O. Sydnes ◽  
Anna Bezos ◽  
Christopher Burns ◽  
Irma Kruszelnicki ◽  
Christopher R. Parish ◽  
...  
Keyword(s):  
Single Crystal ◽  
Building Blocks ◽  
Biological Evaluation ◽  
Enantiomerically Pure ◽  
X Ray ◽  
System 1 ◽  
Synthesis And Biological Evaluation ◽  
Related Compounds

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.

Pyridones – Powerful Precursors for the Synthesis of Alkaloids, Their Derivatives, and Alkaloid-Inspired Compounds

Synthesis ◽  
2019 ◽  
Vol 51 (18) ◽  
pp. 3369-3396 ◽  
Author(s):  
Jacek G. Sośnicki ◽  
Tomasz J. Idzik
Keyword(s):  
Building Blocks ◽  
High Availability ◽  
Ring Formation ◽  
Electrophilic Aromatic Substitution ◽  
Aromatic Substitution ◽  
Ring Fusion ◽  
Naturally Occurring ◽  
Wide Range ◽  
Review Reports ◽  
Related Compounds

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

Robust Synthesis of N-Sulfonylazetidine Building Blocks via Ring Contraction of α-Bromo N-Sulfonylpyrrolidinones

2014 ◽  
Vol 16 (23) ◽  
pp. 6104-6107 ◽  
Author(s):  
Nicolas Kern ◽  
Anne-Sophie Felten ◽  
Jean-Marc Weibel ◽  
Patrick Pale ◽  
Aurélien Blanc
Keyword(s):  
Building Blocks ◽  
Ring Contraction ◽  
Robust Synthesis

New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction

2015 ◽  
Vol 2 (5) ◽  
pp. 497-501 ◽  
Author(s):  
Korry L. Barnes ◽  
Kelly Chen ◽  
Vincent J. Catalano ◽  
Christopher S. Jeffrey
Keyword(s):  
Therapeutic Potential ◽  
Building Blocks ◽  
Biologically Active ◽  
Ring Contraction

Polyhydroxylated piperidines are a functionally rich class of biologically active molecules that have broad therapeutic potential.

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