A Facile Preparation of α-Aryl Carboxylic Acid via One-Flow Arndt–Eistert Synthesis

2015 ◽  
Vol 68 (11) ◽  
pp. 1657 ◽  
Author(s):  
Shinichiro Fuse ◽  
Yuma Otake ◽  
Yuto Mifune ◽  
Hiroshi Tanaka
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Nucleophilic Addition ◽  
Wolff Rearrangement ◽  
Facile Preparation ◽  
Nucleophilic Acyl Substitution

An efficient, one-flow Arndt–Eistert synthesis was demonstrated. A sequence of acid chloride formation–nucleophilic acyl substitution–Wolff rearrangement–nucleophilic addition was performed in a microflow system without isolating any intermediates, which included a potentially explosive compound. The microflow system was made from simple, inexpensive, and readily available instruments and tubes. α-Aryl esters 2a and 2b were prepared in yields of 33 and 23 % (three steps) respectively.

Design, synthesis and evaluation of structurally diverse ortho-acylphenol-diindolylmethane hybrids as anticancer agents

2022 ◽  
Author(s):  
Zhi-Gang Yin ◽  
Xiong-Wei Liu ◽  
Hui-Juan Wang ◽  
Min Zhang ◽  
Xiong-Li Liu ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Anticancer Agents ◽  
Nucleophilic Addition ◽  
Ring Opening ◽  
Building Blocks ◽  
Efficient Synthesis ◽  
Design Synthesis ◽  
Pyrone Ring ◽  
Ring Opening Reaction ◽  
First Time

A highly efficient synthesis of structurally diverse ortho-acylphenol–diindolylmethane hybrids 3 using carboxylic acid-activated chromones as versatile synthetic building blocks is reported here for the first time, through 1,4-nucleophilic addition and followed by a decarboxylation and pyrone ring opening reaction process.

The dimethyl formamide – acyl halide complex and its application to the synthesis of acyl azides

1967 ◽  
Vol 45 (11) ◽  
pp. 1247-1251 ◽  
Author(s):  
Donald E. Horning ◽  
Joseph M. Muchowski
Keyword(s):  
Carboxylic Acid ◽  
Acid Chloride ◽  
Direct Conversion ◽  
Dimethyl Formamide ◽  
Acid Salt ◽  
Acyl Halide ◽  
Acyl Azides ◽  
Selective Formation ◽  
Carboxylic Acid Salt ◽  
Acid Azide

A description of the conditions which favor the formation of the acid chloride – dimethyl formamide complex is given. The utility of the complex is illustrated by its application to the synthesis of acyl azides and, in particular, by the selective formation of 3-bromopropionyl azide from the corresponding acid chloride. The complex also results from a carboxylic acid salt and N,N-dimethyl chloroformiminium chloride, and thus provides an alternative method of effecting the direct conversion of a carboxylic acid into the corresponding acid azide.

Synthesis of amino acid diazoketones

1986 ◽  
Vol 64 (11) ◽  
pp. 2097-2102 ◽  
Author(s):  
George R. Pettit ◽  
Paul S. Nelson
Keyword(s):  
Amino Acid ◽  
Carboxylic Acid ◽  
Acid Chloride ◽  
Low Temperatures ◽  
Oxalyl Chloride ◽  
Acyl Chloride ◽  
Carboxyl Group ◽  
Carboxylic Acid Chloride ◽  
Active Esters ◽  
Active Ester

A study of carboxylic acid → diazoketone conversion was pursued employing the γ-carboxyl group of otherwise protected L-glutamic acids. The Arndt–Eistert route employing carboxylic acid chloride intermediates was found best (52% yield, 5b), performed at very low temperatures employing oxalyl chloride in dimethylformamide–tetrahydrofuran followed by diazomethane at −23 °C. Alternatively, substitution of a mixed carbonic anhydride for the acyl chloride led to very similar yields (57% of 5b) of diazoketones (5). Among a series of active ester intermediates (7) examined, only the ODnp (7d) and SPfp (7f) esters were found to react (23–26% yield), at least partially, with diazomethane. The latter two reactions appear to represent the first such examples employing active esters.

Sign in / Sign up

Export Citation Format

Share Document