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Attempted syntheses of N-confused hydroporphyrins through modified Lindsey routes
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Synthetic Molecular Chemistry.ORCID iD: 0000-0003-2449-102x
2019 (English)In: Journal of Porphyrins and Phthalocyanines, ISSN 1088-4246, E-ISSN 1099-1409, Vol. 23, no 4-5, p. 589-598Article in journal (Refereed) Published
Abstract [en]

Unlike N-confused porphyrins which are well-known and extensively studied tetrapyrroles, N-confused hydroporphyrins are almost unknown, largely because so far they have resisted attempts at rational synthesis. Here, we report our efforts towards the total synthesis of N-confused hydroporphyrins. We have prepared N-confused building blocks analogous to the non-N-confused substrates in the Lindsey synthesis of sparsely substituted chlorins. We have systematically flipped the A, B and C pyrrole rings in the dipyrrolic precursors of the target N-confused macrocycles, preparing in total an N-confused "Western half' (tetrahydrodipyrrin) and two N-confused "Eastern halves" (brominated formyldipyrromethanes). These were subjected to a range of cyclization conditions. While we successfully isolated and identified three macrocyclic products, none of these proved to be the desired N-confused hydroporphyrin.

Place, publisher, year, edition, pages
WORLD SCI PUBL CO INC , 2019. Vol. 23, no 4-5, p. 589-598
Keywords [en]
hydroporphyrins, N-confused tetrapyrroles, chlorins, 2+2 condensation, corrins
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-387228DOI: 10.1142/S1088424619500524ISI: 000468181100026OAI: oai:DiVA.org:uu-387228DiVA, id: diva2:1328312
Funder
Swedish Research CouncilStiftelsen Olle Engkvist ByggmästareAvailable from: 2019-06-20 Created: 2019-06-20 Last updated: 2019-06-20Bibliographically approved

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Xiong, RuishengArkhypchuk, Anna I.Borbas, K. Eszter

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