Vilsmeier cyclization of α-acetyl-α-aroyl ketene-N,S-acetals: direct and efficient synthesis of halogenated pyridin-2(1H)-ones

RSC Advances ◽  
2015 ◽  
Vol 5 (15) ◽  
pp. 11293-11296 ◽  
Author(s):  
Haifeng Yu ◽  
Yongmei Zhang ◽  
Tiechun Li ◽  
Peiqiu Liao ◽  
Quanping Diao ◽  
...  
Keyword(s):  
Synthetic Route ◽  
Efficient Synthesis

An efficient synthetic route to 3-aroyl-5-formyl-4-halo pyridin-2(1H)-ones has been developed via Vilsmeier cyclization of 2-(ethylthio(arylamino)methylene)-1-alkylbutane-1,3-dione.

scholarly journals The Efficient Synthesis of Azasugars from Pentoses

2021 ◽  
Author(s):  
◽  
Michael Meijlink
Keyword(s):  
Clinical Trials ◽  
Biological Properties ◽  
Protecting Groups ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Total Syntheses ◽  
Structural Analogues ◽  
Original Procedure ◽  
Synthetic Routes

<p>Azasugars [e.g., 1-deoxy-aza-xylopyranose (1) Figure 1] are structural analogues of sugars [e.g., α-D-xylopyranose (2)] where the ring oxygen is substituted by a nitrogen atom. The resemblance of azasugars to their carbohydrate counterparts gives them various biological properties, such as the inhibition of glycosidase and glycosyltransferase enzymes, and as such, these compounds have been in clinical trials for the treatment of AIDS, diabetes,and cancer. Synthetic routes to azasugars have often involved the use of protecting groups, and therefore have generally reduced efficiency by requiring additional steps to apply or remove protecting groups or requiring adjustment of stereochemistry during the synthesis. This thesis presents the first example of a synthesis of four sterochemically different piperidine triols through a four-step methodology minimising the use of protecting groups starting from pentoses. The synthesis of D-xylose derived (3R,4r,5S)-piperidine triol was previously obtained in 40% yield over five steps, but was afforded in 45% overall yield over four steps using the methodology described within this thesis. Next, D-ribose derived (3R,4s,5S)-piperidine triol was obtained in 40% overall yield over four steps, which afforded a vast improvement on the previous most efficient synthetic route obtaining the azasugar in 24% yield over four steps. This four-step three-pot methodology has thus allowed for the synthesis of these piperidine triols in overall yields ranging from 4-69%, surpassing previous total syntheses in efficiency and improving overall atom economy. To further probe the applicability of the methodology, N-alkyl analogues (such as butyl-, phenylethyl-, and hydroxyethyl-analogues) of all four different piperidine triols were synthesised in comparable or greater overall yields compared to literature reports without any required adaptation to the original procedure. Included in these N-alkyl analogues are seven novel azasugars which were obtained in overall yields ranging from 6-35%.</p>

Efficient synthesis of polysubstituted 1,5-benzodiazepinone dipeptide mimetics via an Ugi-4CR-Ullmann condensation sequence

Synlett ◽  
2021 ◽  
Author(s):  
Robin Van Den Hauwe ◽  
Mathias Elsocht ◽  
Charlie Hollanders ◽  
Steven Ballet
Keyword(s):  
Building Blocks ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Rapid Construction ◽  
Ligand Free

An efficient three step synthesis towards 3-amino-1,4-benzodiazepin-2-one derivatives is presented. The versatile Ugi-4-component reaction (Ugi-4CR) and Boc-deprotection is followed by a ligand-free Ullmann condensation. This protocol allows the rapid construction of a diverse array of substituted 1,5-benzodiazepinones. Since Ugi-based products are typically limited by their ‘inert’ C-terminal amides, the use of a convertible (‘cleavable’) isocyanide was envisaged and resulted in building blocks that can be made SPPS-compatible. To demonstrate the potential of this novel synthetic route, the design and preparation of novel phenylurea-1,5-bezondiazepin-4(5H)-one dipeptide mimetics with potential CCK2-antagonist properties is reported.

scholarly journals A bio-facilitated synthetic route for nano-structured complex electrode materials

2016 ◽  
Vol 18 (9) ◽  
pp. 2619-2624 ◽  
Author(s):  
Maryam Moradi ◽  
Jae Chul Kim ◽  
Jifa Qi ◽  
Kang Xu ◽  
Xin Li ◽  
...  
Keyword(s):  
Solid State ◽  
Energy Efficient ◽  
Electrode Materials ◽  
Inorganic Materials ◽  
State Solution ◽  
Solid State Reactions ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Wide Range

Bio-facilitated solid state solution: we investigate an energy-efficient synthesis that merges the bio-templated technique and solid-state reactions to produce a wide range of nano-structured complex inorganic materials.

An efficient synthesis of pterosin C and other pterosins

1984 ◽  
Vol 62 (10) ◽  
pp. 1945-1953 ◽  
Author(s):  
Kam-Mui Eva Ng ◽  
Trevor C. McMorris
Keyword(s):  
Acetic Acid ◽  
Acetic Anhydride ◽  
Methyl Ether ◽  
Sodium Acetate ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Trans Isomers ◽  
Cis And Trans Isomers ◽  
Cis And Trans

A versatile synthetic route to pterosins, sesquiterpenoid indanones present in bracken, Pteridiumaquilinum, has been developed. The route is exemplified by the synthesis of (2S,3S)-pterosin C by Friedel–Crafts bisacylation of the methyl ether of 2-(2,6-dimethylphenyl)ethanol with methylmalonyl chloride. Demethylation of the resulting 1,3-indandione and reduction with zinc and acetic acid in the presence of acetic anhydride and sodium acetate afforded a mixture of racemic cis and trans isomers of pterosin C diacetate, which was hydrolysed to the corresponding pterosins. Separation and resolution via the S-(+)-α-phenylbutyric esters gave (2S,3S)-pterosin C and (2R,3R)-pterosin C. Other pterosins were prepared as racemates from the 1,3-indandione.

A Facile and Efficient Synthesis of bis(Imidazo[1,2-a]pyridin-3-yl)methane and vinyl derivatives

2021 ◽  
Vol 18 ◽  
Author(s):  
D.E. Prasada Rao ◽  
M. David Raju ◽  
J. Surendra ◽  
A. Vasu Babu ◽  
P. Eswaraiah ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Trifluoroacetic Acid ◽  
Methyl Chloride ◽  
The Novel ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Vinyl Derivatives

An efficient synthetic route for the novel bis-imdizo[1,2-a]pyridine-3-yl)methane (2a-k) derivatives have been developed using acetic acid and two drops of trifluoroacetic acid at 40-45oC, resulting in 60-72% yields. An attempt to synthesize bis(Imidazo[1,2-a]pyridin-3-yl)methyl chloride derivatives by the reaction between two moles of imidazo[1,2-a]pyridine, one mole of chloroacetaldehyde in acetic acid, and two drops of trifluoroacetic acid was not successful, instead underwent dehydrohalogenation to yield vinyl derivatives (4a-d).

Simple and efficient synthesis of novel N-dichloroacetyl-3,4-dihydro-2H-1,4-benzoxazines

2012 ◽  
Vol 18 (3) ◽  
Author(s):  
Ying Fu ◽  
Li-Hua Qu ◽  
Shan-Shan Zhang ◽  
Fei Ye ◽  
Li-Xia Zhao ◽  
...  
Keyword(s):  
Synthetic Route ◽  
Efficient Synthesis

AbstractAn easy synthetic route to

Efficient synthesis of 4-amino-2,6-dichloropyridine and its derivatives

2016 ◽  
Vol 22 (5) ◽  
Author(s):  
Congming Ma ◽  
Zuliang Liu ◽  
Qizheng Yao
Keyword(s):  
Starting Material ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Important Intermediate

AbstractA facile synthetic route to an important intermediate 4-amino-2,6-dichloropyridine was developed. Oxidation of 2,6-dichloropyridine as a starting material gave pyridine

scholarly journals An Efficient Synthesis of Anti-spasmodic Drug Mebeverine Hydrochloride

2021 ◽  
pp. 325-331
Author(s):  
V. S. R. N. Phanikumar ◽  
G. Veera Raghava Sharma
Keyword(s):  
Irritable Bowel Syndrome ◽  
Active Pharmaceutical Ingredient ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Synthetic Process ◽  
Mebeverine Hydrochloride ◽  
Commercial Process ◽  
Three Stages ◽  
Irritable Bowel

An efficient synthetic process for an antispasmodic drug and active pharmaceutical ingredient of Mebeverine hydrochloride 1 is reported in this communication. It is used for stomach cramps and irritable bowel syndrome (IBS). The treatment for irritable bowel syndrome involves lot of drugs like (Dicyclomine hydrochloride, Linaclotide.etc) available in market, but Mebeverine hydrochloride (1) is most effective than any other drug. Earlier manufacturing 1 process reported yield < 46% and used high volumes of reagents and expensive catalyst. We developed new commercial process for 1 with economically, environmentally favored conditions. Proposed synthetic route contains three stages with overall yield of 77% and Purity by HPLC NLT 99.7%.

The Efficient Synthesis of 2-(3-Carbamoylpyridine-2-yl) nicotinamide Pyridine Salts

2021 ◽  
Vol 18 ◽  
Author(s):  
Lei-Yang Zhang ◽  
Jing-Bo Geng ◽  
Nai-Xing Wang ◽  
Yue-Hua Wu ◽  
Zhan Yan ◽  
...  
Keyword(s):  
Starting Material ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Chiral Compound ◽  
Axial Chirality ◽  
Simple Operation ◽  
Chiral Compounds ◽  
Axially Chiral

: The synthesis of axially chiral compounds has attracted a great deal of attention in the recent years. Herein, an efficient and economical synthetic route has been developed for 2-(3-carbamoylpyridin-2-yl) nicotinamide pyridine salts, an axially chiral compound. The starting material 1,10-phenanthroline has been readily available and 2-(3-carbamoylpyridin-2-yl) nicotinamide pyridine salts have been obtained in moderate to good yields. This protocol features simple operation and easy scalability. In addition, the axial chirality of the products has also been preliminary studied.

scholarly journals Efficient synthesis of fluorescent alkynyl C-nucleosides via Sonogashira coupling for the preparation of DNA-based polyfluorophores

2016 ◽  
Vol 14 (27) ◽  
pp. 6407-6412 ◽  
Author(s):  
Dominik K. Kölmel ◽  
Luzi J. Barandun ◽  
Eric T. Kool
Keyword(s):  
Sonogashira Coupling ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Dna Base ◽  
Facile Preparation

A general synthetic route for the facile preparation of nucleosides with varied fluorophores replacing a DNA base is presented.

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