Synthesis of 2-aryl-1,3-benzoselenazoles from bis(2- aminophenyl) diselenides and carboxylic acids using PBu3

Synthesis of 2-aryl-1,3-benzoselenazoles from bis(2- aminophenyl) diselenides and carboxylic acids using PBu3

Radatz, Cátia S.; Rampon, Daniel S.; Balaguez, Renata A.; Alves, Diego; Schneider, Paulo H.

Abstract:

The investigation about different seleniumcontaining heterocyclic compounds has expanded rapidly during last years. Furthermore, substituted benzochalcogenazole systems have presented also interesting pharmaceutical properties. Besides, the synthesis of 2-substituted-1,3-benzothiazoles have attracted much attention according to their notably photophysical properties. Our continuing interest on the synthesis of organoselenium compounds prompted us to explore a general procedure to obtain 2-substituted 1,3-benzoselenazoles from bis(2-aminophenyl) diselenide (1a) and carboxylic acids (2a-m), using tributylphosphine in toluene under conventional heating or microwave irradiation (scheme 1).

The investigation about different seleniumcontaining heterocyclic compounds has expanded rapidly during last years. Furthermore, substituted benzochalcogenazole systems have presented also interesting pharmaceutical properties. Besides, the synthesis of 2-substituted-1,3-benzothiazoles have attracted much attention according to their notably photophysical properties. Our continuing interest on the synthesis of organoselenium compounds prompted us to explore a general procedure to obtain 2-substituted 1,3-benzoselenazoles from bis(2-aminophenyl) diselenide (1a) and carboxylic acids (2a-m), using tributylphosphine in toluene under conventional heating or microwave irradiation (scheme 1).

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013915175028

Referências bibliográficas

• [1] 1 (a) Goodman, C. Nature Chem. Bio. 2013, 9, 214. (b) Koehnke, J.; et al.
• [2] Chem. Bio. Chem. 2013, 5, 564.
• [3] 2 Tareq, M. et. al (Eds). Topics in Heterocyclic Chemistry, Bioactive
• [4] Heterocycles III. Springer, Berlin, 2007.
• [5] 3 Gupta, A.; Rawat, S. J. Curr. Pharm. Res. 2010, 3, 13.
• [6] 4 Radatz, C.; et al. Tetrahedron. 2013, 69 1316.
• [7] 5 Kappe, C. O.; et. al (Eds.). Practical Microwave Synthesis for Organic
• [8] Chemists: Strategies, Instruments, and Protocols. Wiley-VCH, Weinheim,
• [9] 2009.

Como citar:

Radatz, Cátia S.; Rampon, Daniel S.; Balaguez, Renata A.; Alves, Diego; Schneider, Paulo H.; "Synthesis of 2-aryl-1,3-benzoselenazoles from bis(2- aminophenyl) diselenides and carboxylic acids using PBu3", p-261-261. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_2013915175028