The Preparation of Pyrrole-2-carboxylates From Vinyl Sulfones

Arnold, D. P.; Burgess‐Dean, L.; Hubbard, Jeremiah W.; Rahman, M. A.

doi:10.1071/ch9940969

Cited by 27 publications

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“…Compound 2 was further transformed into vinyl sulfone 3 via the sequence of published reactions ( b1, c1 ) . Vinyl sulfone 3 was reacted with ethyl isocyanoacetate in the modified Barton−Zard synthesis , ( d1 ) to yield pyrrole ester 4 , which was converted into pyrrole 5 upon reflux with KOH in ethylene glycol ( e1 ). Pyrrole 5 without isolation was introduced into the Lindsey condensation with aromatic aldehydes ( f1 ), yielding porphyrins 6a , b .…”

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confidence: 99%

Synthesis of Symmetrical Tetraaryltetranaphtho[2,3]porphyrins

et al. 2005

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A new method of synthesis of meso-tetraaryltetranaphtho[2,3]porphyrins (Ar4TNP) has been developed. Ar4TNPs with peripheral functional groups are obtained by oxidative aromatization of meso-tetraarylporphyrins in which pyrrole units are fused with either octahydro- or dihydronaphthalene moieties. These precursor porphyrins are synthesized in four to five steps from readily available starting materials, such as naphthalene or 1,4-benzoquinone. The pathway originating in dihydronaphthalene, i.e., the "dialine" route, was found to be superior to the alternative "octaline"route in that it (1) enables the shortening of the overall reaction sequence, (2) has a broader scope in terms of the peripheral substitution in Ar4TNPs, and (3) affords higher yields of the target porphyrins. Pd complexes of the synthesized Ar4TNPs exhibit remarkably strong absorption bands at 710-720 nm (epsilon approximately 200,000 M(-1) cm(-1)) and phosphoresce at room temperature with moderate quantum yields (phi = 2-3%, lambda(max) = 900-1000 nm). The absorption maxima of naphthoporphyrins substituted with eight methoxy groups (Ar4TNP(OMe)8) were found to be about 15-20 nm red shifted compared to the corresponding maxima of unsubstituted Ar4TNPs. The X-ray crystallographic data suggest that these spectral shifts are caused not by the differences in nonplanar distortions of the macrocycles but by the purely electronic effects of the substituents.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Symmetrical Tetraaryltetranaphtho[2,3]porphyrins

et al. 2005

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“…In the first route, 1 was converted ( a1 ) into cis -Δ 2 -octaline 2 , which was transformed into vinyl sulfone 3 via the sequence of published reactions ( b1, c1 ) . Vinyl sulfone 3 reacted with ethyl isocyanoacetate in the modified Barton-Zard synthesis , ( d1 ), giving pyrrole ester 4 , which was converted into pyrrole 5 upon reflux with KOH in ethylene glycol ( e1 ). Pyrrole 5 without isolation was introduced into Lindsey-type condensation ( f1 ), yielding porphyrin 6 in 44% yield.…”

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Novel Route to Functionalized Tetraaryltetra[2,3]naphthaloporphyrins via Oxidative Aromatization

et al. 2003

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A novel general route to substituted meso-tetraaryltetra[2,3]naphthaloporphyrins (Ar(4)TNP) and meso-tetraaryloctamethoxytetra[2,3]naphthaloporphyrins (Ar(4)(MeO)(8)TNP) via oxidative aromatization of nonaromatically fused porphyrin precursors is described. Ar(4)(MeO)(8)TNPs exhibit more red-shifted absorption bands than Ar(4)TNPs and differ dramatically in solubility. The first X-ray crystallographic structure of tetranaphthaloporphyrin, i.e., PdAr(4)TNP (Ar = 4-MeO(2)CC(6)H(4)), revealed that the degree of nonplanar distortion of this macrocycle is only slightly higher than that of the homologous tetrabenzoporphyrins (Ar(4)TBP).

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Synthesis of Pyrroles and Their Derivatives from Isocyanides

Ono

Okujima

2012

Isocyanide Chemistry

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The Preparation of Pyrrole-2-carboxylates From Vinyl Sulfones

Cited by 27 publications

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Synthesis of Symmetrical Tetraaryltetranaphtho[2,3]porphyrins

Synthesis of Symmetrical Tetraaryltetranaphtho[2,3]porphyrins

Novel Route to Functionalized Tetraaryltetra[2,3]naphthaloporphyrins via Oxidative Aromatization

Synthesis of Pyrroles and Their Derivatives from Isocyanides

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