Chloroacetic acid-promoted heterocyclic reactions: Efficient preparation of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones

Authors

  • Elham Fereidooni Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
  • Jasem Aboonajmi Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
  • Mojtaba Lashakri Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
  • Naeime Khorshidi Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
  • Nasrin Mahmoudabadi Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
  • Nourallah Hazeri Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
  • Sajjad Salahi Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran
Abstract:

Facile and versatile procedures have been explored for the synthesis of tetrahydropyridines and 2,3-dihydroquinazolin-4(1H)-ones. These protocols employ the one-pot multi-component condensation of arylaldehydes and aromatic amines with β-keto esters and isatoic anhydride in chloroacetic acid, respectively. The reactions proceeded smoothly to generate the corresponding products in high yield. We have found that the use of chloroacetic acid as catalyst results in a remarkable beneficial effect on the reaction, allowing it to be performed without the need of any co-catalyst, which is the case in other similar reported methodologies. In addition, the preparation of 2,3-dihydro-4(1H)-quinazolinones derivatives from the reaction of arylaldehydes and anthranilamide in the presence of mentioned catalyst is reported.

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

chloroacetic acid-promoted heterocyclic reactions: efficient preparation of tetrahydropyridines and 2,3-dihydroquinazolin-4(1h)-ones

facile and versatile procedures have been explored for the synthesis of tetrahydropyridines and 2,3-dihydroquinazolin-4(1h)-ones. these protocols employ the one-pot multi-component condensation of arylaldehydes and aromatic amines with β-keto esters and isatoic anhydride in chloroacetic acid, respectively. the reactions proceeded smoothly to generate the corresponding products in high yield. we...

full text

Microwave Irradiation Promoted Reactions of Orthoesters with Carboxylic Acid Hydrazides. Preparation of 1,3,4-Oxadiazoles

Rapid and highly efficient synthesis of 2- or 2,5-substituted 1,3,4-oxadiazoles by the condensation of aryl carboxylic acid hydrazides and orthoesters can be achieved under microwave irradiation using an unmodified commercial over in unsealed vessels.

full text

Microwave Irradiation Promoted Reactions of Benzoxazin-4-Ones with Primary Amines. Preparation of 4(2=3H)-Quinazolinones

An efficient synthesis of 3-substituted or 2,3-disubstituted 4(3H)-quinazolinones from benzoxazin-4-ones and primary amines under microwave irradiation in unsealed vessels is described.

full text

Preparation and Reactions of Heterocyclic Compounds II

Commercial preparation of furan proceeds by way of the aldehyde, furfural, which in turn is generated from pentose containing raw materials like corncobs, as shown in the uppermost equation below. Similar preparations of pyrrole and thiophene are depicted in the second row equations. Equation 1 in the third row illustrates a general preparation of substituted furans, pyrroles and thiophenes fro...

full text

My Resources

Save resource for easier access later

Save to my library Already added to my library

{@ msg_add @}


Journal title

volume 5  issue 3

pages  245- 252

publication date 2015-09-01

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