One-pot synthesis of ferrocene-containing 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), cyclic ketones and ferrocene carboxylic acid

Authors

  • Morteza Rouhani Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran
Abstract:

Reactions of N-isocyaniminotriphenylphosphorane with a cyclic ketone in the presence of ferrocene carboxylic acid proceeded smoothly at room temperature and in neutral conditions to afford ferrocene-containing 1,3,4-oxadiazole derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, 1HNMR, and 13CNMR spectra. The method offers a mild, simple, and efficient route for the preparation oreaction of N-isocyaniminotriphenylphosphorane with cyclic ketones in the presence of ferrocene carboxylic acid proceeded smoothly at room temperature and in neutral conditions to afford ferrocene-containing 1,3,4-oxadiazole derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, 1HNMR, and 13CNMR spectra. f sterically congested ferrocene-containing 1,3,4-oxadiazole derivatives from cyclic ketones, N-isocyaniminotriphenylphosphorane (Ph3PNNC) and ferrocene carboxylic acid. Its ease of workup, high yields and fairy mild reaction conditions make it a useful addition to modern synthetic methodologies.

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

One-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane (Ph3PNNC), a primary amine, a carboxylic acid and cinnamaldehyde

The imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the N-isocyaniminotriphenylphosphorane (Ph3PNNC) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. The 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were comp...

full text

one-pot, four-component synthesis of fully substituted 1,3,4-oxadiazole derivatives from n-isocyaniminotriphenylphosphorane (ph3pnnc), a primary amine, a carboxylic acid and cinnamaldehyde

the imine intermediate generated by the addition of primary amine to the cinnamaldehyde is trapped by the n-isocyaniminotriphenylphosphorane (ph3pnnc) and a carboxylic acid, and leads to the formation of the corresponding iminophosphorane intermediate. the 1,3,4-oxadiazole derivatives are formed via intramolecular aza-wittig reaction of the iminophosphorane intermediate. the reactions were comp...

full text

Preparation of sterically congested 1,3,4-oxadiazole derivatives from N-isocyaniminotriphenylphosphorane, aromatic acids, cyclopentanone and primary amines

Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone have been studied in the presence of aromatic carboxylic acids and primary amines, proceeds smoothly at room temperature under neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives by an intramolecular Aza-Wittig cyclization in CH2Cl2 in excellent yields. The structures of the products were deduced from...

full text

One-pot Three-Component Synthesis of Dihydroquinoxalin-2-amines Containing a Ferrocene unit with the Potential of Biological and Pharmacological Activities

A three-component reaction between 1,2-phenylenediamine, ferrocenecarbaldehyde, and isocyanides in the presence of a catalytic amount of p-toluenesulfonic acid for the synthesis of 3,4-dihydroquinoxalin-2-amine derivatives containing a ferrocene unit is reported. This approach is an effective procedure because the products have a broad spectrum of biological and pharmacological activities such ...

full text

Ring Rotation in Ferrocene and Ferrocene-containing Polymers

Ferrocene is an organometallic molecular sandwich complex with an iron atom coordinated between two cyclopentadienyl rings. The reorientation of these rings in a process of rotational jump diffusion between multiple equilibrium sites on a circle is investigated using quasielastic neutron time of flight and backscattering spectroscopy experiments. Existing results on the ring rotation in bulk, c...

full text

Helically chiral ferrocene peptides containing 1'-aminoferrocene-1-carboxylic acid subunits as turn inducers.

We present a detailed structural study of peptide derivatives of 1'-aminoferrocene-1-carboxylic acid (ferrocene amino acid, Fca), one of the simplest organometallic amino acids. Fca was incorporated into di- to pentapeptides with D- and L-alanine residues attached to either the carboxy or amino group, or to both. Crystallographic and spectroscopic studies (circular dicroism (CD), IR, and NMR) o...

full text

My Resources

Save resource for easier access later

Save to my library Already added to my library

{@ msg_add @}


Journal title

volume 7  issue Issue 1, pp. 1-124

pages  117- 124

publication date 2019-01-01

By following a journal you will be notified via email when a new issue of this journal is published.

Hosted on Doprax cloud platform doprax.com

copyright © 2015-2023