English
 
User Manual Privacy Policy Disclaimer Contact us
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives: new synthetic routes and crystal structures

Mallah, E., Sweidan, K., Engelmann, J., Steimann, M., Kuhn, N., & Maier, M. (2012). Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives: new synthetic routes and crystal structures. Tetrahedron, 68(4), 1005-1010. doi:10.1016/j.tet.2011.11.093.

Item is

Basic

show hide
Item Permalink: http://hdl.handle.net/21.11116/0000-0001-8A88-A Version Permalink: http://hdl.handle.net/21.11116/0000-0001-8A89-9
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Mallah, E, Author
Sweidan, K, Author              
Engelmann, J1, 2, Author              
Steimann, M, Author
Kuhn, N, Author
Maier, ME, Author
Affiliations:
1Department High-Field Magnetic Resonance, Max Planck Institute for Biological Cybernetics, Max Planck Society, ou_1497796              
2Max Planck Institute for Biological Cybernetics, Max Planck Society, Spemannstrasse 38, 72076 Tübingen, DE, ou_1497794              

Content

show
hide
Free keywords: -
 Abstract: We describe simple, convenient and high-yielding nucleophilic substitution reactions to synthesize new derivatives of 1,3-dimethylbarbituric acid (1a). Based on its active C5 position, condensing 1a with sulfuryl chloride gives the corresponding 5,5-dichloro-1,3-dimethylbarbituric acid (13). The latter was reacted with silver nitrite and potassium cyanide to afford 5-chloro-5-nitro-1,3-dimethylbarbituric acid (14) and 5-cyano-1,3-dimethylbarbiturate (17), respectively. Furthermore, by employing the nucleophilic character of 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (8) the obtained compounds 13 and 14 have been converted to 2-chloro-1,3-diisopropyl-4,5-dimethyl-1H-imidazol-3-ium-1,3-dimethyl-5-nitro-1,3-dimethylbarbiturate (18) and 1,3-dimethylbarbituric acid trimer (21), respectively. X-ray structures for compounds 13, 14, 17, 18 and 21 were determined.

Details

show
hide
Language(s):
 Dates: 2012-01
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: DOI: 10.1016/j.tet.2011.11.093
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Tetrahedron
  Other : Tetrahedron : the international journal for the rapid publication of full original research papers and critical reviews in organic chemistry
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Kidlington : Elsevier Science
Pages: - Volume / Issue: 68 (4) Sequence Number: - Start / End Page: 1005 - 1010 Identifier: ISSN: 0040-4020
CoNE: https://pure.mpg.de/cone/journals/resource/00404020