Synthesis of 3,4-dibromo-1H-pyrrole-2-carbaldehyde: a building block for preparation of tetrabromobacteriochlorins

Synthesis of 3,4-dibromo-1H-pyrrole-2-carbaldehyde: a building block for preparation of tetrabromobacteriochlorins

Assis, Francisco F. de; Brocksom, Timothy J.; Oliveira., Kleber T. de

Abstract:

Bacteriochlorins are porphyrin derivatives in which two of the double bonds of the porphyrin ring system have been reduced (Figure 1). The bacteriochlorins have found many applications in photomedicine and materials science. The synthesis of these compounds represents a challenge due to the tendency to re-oxidize back to the corresponding chlorin or porphyrin. Problems of separation and purification are also common due to the formation of complex mixtures. Lindsey’s group has developed an efficient approach to synthesize stable substituted bacteriochlorins, without formation of complex product mixtures. In this work, we describe the synthesis of a suitably functionalized pyrrole, which is to be used as a building block for the synthesis of bacteriochlorins, through Lindsey’s methodology.

Bacteriochlorins are porphyrin derivatives in which two of the double bonds of the porphyrin ring system have been reduced (Figure 1). The bacteriochlorins have found many applications in photomedicine and materials science. The synthesis of these compounds represents a challenge due to the tendency to re-oxidize back to the corresponding chlorin or porphyrin. Problems of separation and purification are also common due to the formation of complex mixtures. Lindsey’s group has developed an efficient approach to synthesize stable substituted bacteriochlorins, without formation of complex product mixtures. In this work, we describe the synthesis of a suitably functionalized pyrrole, which is to be used as a building block for the synthesis of bacteriochlorins, through Lindsey’s methodology.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_2013913103524

Referências bibliográficas

• [1] 1 Taniguchi, M.; Cramer, D. L.; Bhise, A. D.; Kee, H. L.; Bocian, D. F.;
• [2] Holten, D.; Lindsey, J. S. New J. Chem. 2008, 32, 947.
• [3] 2 Huang, Y.-Y.; Mroz, P.; Zhiyentayev, T.; Sharma, S. K.;
• [4] Balasubramanian, T.; Ruzié, C.; Krayer, M.; Fan, D.; Borbas, K. E.; Yang,
• [5] E.; Kee, H. L.; Kirmaier, C.; Diers, J. R.; Bocian, D. F.; Holten, D.; Lindsey,
• [6] J. S.; Hamblin, M. R. J. Med. Chem. 2010, 53, 4018.
• [7] 3 a) Kim, H.-L.; Lindsey, J. S. J. Org. Chem. 2005, 70, 5475. b) Krayer, M.;
• [8] Ptaszek, M.; Kim, H.-L.; Meneely, K. L.; Fan, D.; Secor, K.; Lindsey, J. S. J.
• [9] Org. Chem. 2010, 75, 1016.

Como citar:

Assis, Francisco F. de; Brocksom, Timothy J.; Oliveira., Kleber T. de; "Synthesis of 3,4-dibromo-1H-pyrrole-2-carbaldehyde: a building block for preparation of tetrabromobacteriochlorins", p-221-221. 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_2013913103524