Synthesis of Substituted Selenolo[3,2-d][1,2,3]triazines
and [1,3]Selenazolo[4,5-d][1,2,3]triazines

Enrico Perspicace; David Thomae; Grégory Hamm; Stéphanie Hesse; Gilbert Kirsch; Pierre Seck

doi:10.1055/s-0029-1216950

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2009(20): 3472-3476
DOI: 10.1055/s-0029-1216950

PAPER

Synthesis of Substituted Selenolo[3,2-d][1,2,3]triazines and [1,3]Selenazolo[4,5-d][1,2,3]triazines

Enrico Perspicace^a, David Thomae^a, Grégory Hamm^b, Stéphanie Hesse*^a, Gilbert Kirsch^a, Pierre Seck^c
^a Laboratoire d’Ingénierie Moléculaire et Biochimie Pharmacologique, Institut Jean Barriol FR CNRS 2843, Université Paul Verlaine - Metz, 1 Boulevard Arago, 57070 Metz Technopôle, France
Fax: +33(3)87325801; e-Mail: hesse@univ-metz.fr;
^b Laboratoire de Spectrométrie de Masse et de Chimie Laser, Institut Jean Barriol FR CNRS 2843, Université Paul Verlaine - Metz, 1 Boulevard Arago, 57070 Metz Technopôle, France
^c Laboratoire de chimie, Faculté des sciences, de la Technologie et de la Communication, Université du Luxembourg, 162a, avenue de la Faïencerie, 1511 Luxembourg, Grand-Duché de Luxembourg

Further Information

Publication History

Received 20 May 2009
Publication Date:
21 August 2009 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

5-Substituted 3-amino-selenophene-2-carbonitriles and 2-substituted 4-amino-1,3-selenazole-5-carbonitriles were reacted with sodium nitrite in hydrochloric acid to give chloroselenolotriazines and chloroselenazolotriazines. These compounds were then subjected to S_NAr reactions with secondary amines under microwave irradiation.

Key words

heterocycles - selenium - microwave - triazines

References

1a Thomae D. Kirsch G. Seck P. Synthesis 2007, 1027

Google Scholar
1b Seck P. Thomae D. Kirsch G. J. Heterocycl. Chem. 2008, 45: 853

Google Scholar
1c Thomae D. Kirsch G. Seck P. Kaminski T. Synthesis 2007, 2153

Google Scholar
2 Thomae D. Kirsch G. Seck P. Synthesis 2008, 1600

Article in Thieme Connect Google Scholar
3 Thomae D. Perspicace E. Hesse S. Kirsch G. Seck P. Tetrahedron 2008, 64: 9309

Crossref Google Scholar
4 Hesse S. Perspicace E. Kirsch G. Tetrahedron Lett. 2007, 48: 5261

Crossref Google Scholar
5 Hesse S. Chenet C. Thomae D. Kirsch G. Synthesis 2009, 1204

Article in Thieme Connect Google Scholar
6 Manfredini S. Bazzanini R. Baraldi PG. Guarneri M. Simoni D. Marongiu ME. Pani A. Tramontano E. La Colla P. J. Med. Chem. 1992, 35: 917

Crossref PubMed Google Scholar
7 Migawa MT. Drach JC. Townsend LB. J. Med. Chem. 2005, 48: 3840

Crossref Google Scholar
8 Quintela JM. Peinador C. Veiga MC. Botana LM. Alfonso A. Riguera R. Eur. J. Med. Chem. 1998, 33: 887

Crossref Google Scholar
9 Quintela JM. Peinador C. Gonzales L. Iglesias R. Parama A. Alvarez F. Sanmartin ML. Riguera R. Eur. J. Med. Chem. 2003, 38: 265

Crossref Google Scholar
10a Hunt JCA. Briggs E. Clarke ED. Whittingham WG. Bioorg. Med. Chem. Lett. 2007, 17: 5222

Google Scholar
10b Paronikyan EG. Noravyan AS. Akopyan SF. Arsenyan FG. Stepanyan GM. Garibdzhanyan BT. Pharm. Chem. J. 2006, 40: 293

Google Scholar
11 Migawa MT. Townsend LB. J. Org. Chem. 2001, 66: 4776

Crossref Google Scholar
12 Moyano EL. Colomer JP. Yranzo GI. Eur. J. Med. Chem. 2008, 3377

Google Scholar
13 Abdel-Hafez ShH. Russ. J. Org. Chem. 2005, 41: 396

Crossref Google Scholar
14 Thomae D. Perspicace E. Xu Z. Henryon D. Schneider S. Hesse S. Kirsch G. Seck P. Tetrahedron 2009, 65: 2982

Crossref Google Scholar