Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

Sven M. Baum; Andrés A. Trabanco; Antonio Garrido Montalban; Aaron S. Micallef; Chang Zhong; Hubert G. Meunier; Klaus Suhling; David Phillips; Andrew J.P. White; David J. Williams; Anthony G.M. Barrett; Brian M. Hoffman

doi:10.1021/jo026484u

Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

Sven M. Baum, Andrés A. Trabanco, Antonio Garrido Montalban, Aaron S. Micallef, Chang Zhong, Hubert G. Meunier, Klaus Suhling, David Phillips, Andrew J.P. White, David J. Williams, Anthony G.M. Barrett^*, Brian M. Hoffman

^*Corresponding author for this work

Chemistry

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80 Scopus citations

Abstract

The novel five- and seven-membered ring appended aminoporphyrazines 3 and 12 have been prepared via mixed Linstead macrocyclization. The structures of both have been unequivocally established by X-ray crystallographic studies. Reductive deselenation of selenadiazole 3 in the presence of 9,10-phenanthrenequinone or 2,3-butanedione results in the formation of pyrazines 6a,b, whereas oxidation of porphyrazine 12 gave the corresponding seco derivative 14. seco-Porphyrazine 14 mediates the generation of singlet oxygen with a quantum yield of 0.74.

Original language	English (US)
Pages (from-to)	1665-1670
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	68
Issue number	5
DOIs	https://doi.org/10.1021/jo026484u
State	Published - Mar 7 2003

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo026484u

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Baum, S. M., Trabanco, A. A., Montalban, A. G., Micallef, A. S., Zhong, C., Meunier, H. G., Suhling, K., Phillips, D., White, A. J. P., Williams, D. J., Barrett, A. G. M., & Hoffman, B. M. (2003). Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings. Journal of Organic Chemistry, 68(5), 1665-1670. https://doi.org/10.1021/jo026484u

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title = "Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings",

abstract = "The novel five- and seven-membered ring appended aminoporphyrazines 3 and 12 have been prepared via mixed Linstead macrocyclization. The structures of both have been unequivocally established by X-ray crystallographic studies. Reductive deselenation of selenadiazole 3 in the presence of 9,10-phenanthrenequinone or 2,3-butanedione results in the formation of pyrazines 6a,b, whereas oxidation of porphyrazine 12 gave the corresponding seco derivative 14. seco-Porphyrazine 14 mediates the generation of singlet oxygen with a quantum yield of 0.74.",

author = "Baum, {Sven M.} and Trabanco, {Andr{\'e}s A.} and Montalban, {Antonio Garrido} and Micallef, {Aaron S.} and Chang Zhong and Meunier, {Hubert G.} and Klaus Suhling and David Phillips and White, {Andrew J.P.} and Williams, {David J.} and Barrett, {Anthony G.M.} and Hoffman, {Brian M.}",

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T1 - Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

AU - Baum, Sven M.

AU - Trabanco, Andrés A.

AU - Montalban, Antonio Garrido

AU - Micallef, Aaron S.

AU - Zhong, Chang

AU - Meunier, Hubert G.

AU - Suhling, Klaus

AU - Phillips, David

AU - White, Andrew J.P.

AU - Williams, David J.

AU - Barrett, Anthony G.M.

AU - Hoffman, Brian M.

PY - 2003/3/7

Y1 - 2003/3/7

N2 - The novel five- and seven-membered ring appended aminoporphyrazines 3 and 12 have been prepared via mixed Linstead macrocyclization. The structures of both have been unequivocally established by X-ray crystallographic studies. Reductive deselenation of selenadiazole 3 in the presence of 9,10-phenanthrenequinone or 2,3-butanedione results in the formation of pyrazines 6a,b, whereas oxidation of porphyrazine 12 gave the corresponding seco derivative 14. seco-Porphyrazine 14 mediates the generation of singlet oxygen with a quantum yield of 0.74.

AB - The novel five- and seven-membered ring appended aminoporphyrazines 3 and 12 have been prepared via mixed Linstead macrocyclization. The structures of both have been unequivocally established by X-ray crystallographic studies. Reductive deselenation of selenadiazole 3 in the presence of 9,10-phenanthrenequinone or 2,3-butanedione results in the formation of pyrazines 6a,b, whereas oxidation of porphyrazine 12 gave the corresponding seco derivative 14. seco-Porphyrazine 14 mediates the generation of singlet oxygen with a quantum yield of 0.74.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

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CCDC 200087: Experimental Crystal Structure Determination

CCDC 200086: Experimental Crystal Structure Determination

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Synthesis and reactions of aminoporphyrazines with annulated five- and seven-membered rings

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CCDC 200087: Experimental Crystal Structure Determination

CCDC 200086: Experimental Crystal Structure Determination

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