Synthetic approaches to 5:8-fused heterocyclic systems. A novel rearrangement during the synthesis of imidazo[4,5-e][1,2,4]triazocine ring system

Article abstract of DOI:10.1080/15257779508012373

The attempted ring-closure of 4-amino-1-benzyl-5-[(N²-benzyl-N²- methoxycarbonyl)hydrazinomethylenecarbonyl]imidazole (5b) in sodium hydride/dimethyl sulfoxide at 50-60 °C afforded 1,7-dibenzylxanthine (6) instead of the anticipated 5:8-fused heterocycle 4b. A tentative reaction pathway has been proposed for the observed transformation.

Full text of DOI:10.1080/15257779508012373

This article was downloaded by: [Columbia University]
On: 11 November 2014, At: 10:47
Publisher: Taylor & Francis
Informa Ltd Registered in England and Wales Registered Number: 1072954 Registered
office: Mortimer House, 37-41 Mortimer Street, London W1T 3JH, UK
Nucleosides and Nucleotides
Publication details, including instructions for authors and
subscription information:
http://www.tandfonline.com/loi/lncn19
Synthetic Approaches to 5:8-Fused
Heterocyclic Systems. A Novel
Rearrangement During the Synthesis of
Imidazo[4,5-e][1,2,4]triazocine Ring
System
Friedrich N. Burnett a & Ramachandra S. Hosmane a
a Laboratory for Drug Design and Synthesis Department of Chemistry
and Biochemistry , University of Maryland Baltimore County ,
Baltimore, Maryland, 21228
Published online: 16 Feb 2007.
To cite this article: Friedrich N. Burnett & Ramachandra S. Hosmane (1995) Synthetic Approaches
to 5:8-Fused Heterocyclic Systems. A Novel Rearrangement During the Synthesis of Imidazo[4,5-e]
[1,2,4]triazocine Ring System, Nucleosides and Nucleotides, 14:3-5, 325-328
To link to this article: http://dx.doi.org/10.1080/15257779508012373
PLEASE SCROLL DOWN FOR ARTICLE
Taylor & Francis makes every effort to ensure the accuracy of all the information (the
“Content”) contained in the publications on our platform. However, Taylor & Francis,
our agents, and our licensors make no representations or warranties whatsoever as to
the accuracy, completeness, or suitability for any purpose of the Content. Any opinions
and views expressed in this publication are the opinions and views of the authors,
and are not the views of or endorsed by Taylor & Francis. The accuracy of the Content
should not be relied upon and should be independently verified with primary sources
of information. Taylor and Francis shall not be liable for any losses, actions, claims,
proceedings, demands, costs, expenses, damages, and other liabilities whatsoever or
howsoever caused arising directly or indirectly in connection with, in relation to or arising
out of the use of the Content.
This article may be used for research, teaching, and private study purposes. Any
substantial or systematic reproduction, redistribution, reselling, loan, sub-licensing,
systematic supply, or distribution in any form to anyone is expressly forbidden. Terms &
Conditions of access and use can be found at http://www.tandfonline.com/page/terms-
and-conditions