Synthesis of sapphyrins via a ‘3+1+1’ procedure

Шевчук, С. В.; Davis, Julian M.; Sessler, Jonathan L.

doi:10.1016/s0040-4039(01)00198-8

Cited by 54 publications

(27 citation statements)

References 18 publications

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“…Sapphyrin Synthesis PCI-2000 was prepared using the ''3+1+1'' procedure as described in the literature (10). The synthesis of PCI-2050 and its derivatives (PCI-2051, PCI-2052, and PCI-2053; see Fig.…”

Section: Methodsmentioning

confidence: 99%

Tumor localization and antitumor efficacy of novel sapphyrin compounds

Naumovski

Sirisawad

Lecane

et al. 2006

Molecular Cancer Therapeutics

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Section: Methodsmentioning

confidence: 99%

Tumor localization and antitumor efficacy of novel sapphyrin compounds

Naumovski

Sirisawad

Lecane

et al. 2006

Molecular Cancer Therapeutics

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“…Recently, a synthesis of sapphyrins was reported that does not require the use of a preformed bipyrrolic moiety [85] and enabled sapphyrins 76 a-d to be obtained in yields ranging from 28 to 34 % (Scheme 19) by condensing tripyrranedialdehydes 74 a,b with two equivalents of pyrroles 75 a-c under acidic conditions, followed by oxidation with DDQ. As expected from such a reaction sequence, the corresponding porphyrins were also isolated in approximately 10 % yield.…”

Section: Synthesis Of Sapphyrins By a 3+1+1 Proceduresmentioning

confidence: 99%

Synthetic Expanded Porphyrin Chemistry

2003

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Expanded porphyrins are synthetic analogues of the porphyrins, and differ from these and other naturally occurring tetrapyrrolic macrocycles by containing a larger central core with a minimum of 17 atoms, while retaining the extended conjugation features that are a hallmark of these quintessential biological pigments. The result of core expansion is to produce systems with novel spectral and electronic features, interesting and, often unprecedented, cation-coordination properties, and, in many cases, an ability to bind anions in certain protonation states. Also adding to the appeal of expanded porphyrins is their central role in addressing issues of aromaticity. In many cases, they also display structural features, such as decidedly nonplanar "figure-eight" motifs, that have no antecedents in the chemistry of porphyrins or related macrocyclic compounds. In this Review, the various synthetic approaches now being employed to produce expanded porphyrins as well as their various applications-related aspects are discussed.

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“…Found: C,72.41;H,6.22;S,20.92. 4.4.2. 3,3 0 ,4,4 0 -Tetraethyl-2,2 0 -bi-1H-pyrrole (21b) 67 . A colorless solid, mp 90-92 C (hexane/AcOEt).…”

Section: 2unclassified