Azaporphyrins: structure of the reaction centre and reactions of complex formation

Stuzhin, Pavel A.; Khelevina, O. G.

doi:10.1016/0010-8545(94)01126-5

Cited by 65 publications

(55 citation statements)

References 59 publications

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“…Porphyrazines in general, however, have so far been comparatively much less studied [3][4][5][6][7]. Hence great possibility is presently offered for the synthesis and investigation of new classes of such macrocycles.…”

Section: Introductionmentioning

confidence: 99%

Tetrakis(selenodiazole)porphyrazines 1: Tetrakis(selenodiazole)porphyrazine and its Mg(II) and Cu(II) Derivatives. Evidence for their Conversion to Tetrakis(pyrazino)porphyrazines through Octaaminoporphyrazines

Bauer

Ercolani

Galli

et al. 1999

J. Porphyrins Phthalocyanines

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The new phthalocyanine-like macrocycle tetrakis(selenodiazole)porphyrazine, TSeDPzH 2, and its Mg ( II ) and Cu ( II ) complexes have been prepared and their general, spectroscopic (IR, UV-vis), and magnetic properties investigated. It has been observed that the peripheral selenodiazole rings of the TSeDPz skeleton can be opened by the action of H 2 S , with release of the Se atoms and formation of a new macrocycle, i.e. octaaminoporphyrazine, which is easily converted into tetrakis(pyrazino)porphyrazine derivatives.

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Section: Introductionmentioning

confidence: 99%

Tetrakis(selenodiazole)porphyrazines 1: Tetrakis(selenodiazole)porphyrazine and its Mg(II) and Cu(II) Derivatives. Evidence for their Conversion to Tetrakis(pyrazino)porphyrazines through Octaaminoporphyrazines

Bauer

Ercolani

Galli

et al. 1999

J. Porphyrins Phthalocyanines

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“…They form part of the molecular structure of many alkaloids and natural macrocycles (hemes, bile pigments, chlorophylls, etc.) and are used in constructing attractive materials such as porphyrins, [1] expanded porphyrins and their heterologs, [2] porphyrazines, [3] and open-chain polypyrroles. [4] Scheme 1.…”

mentioning

confidence: 99%

A New Access to 2-(Alkylamino)- and 2-(Arylamino)pyrroles by Addition of Isocyanides to Protonated 1-Azabutadienes

Marchand

Morel²,

Sinbandhit

1999

Eur. J. Org. Chem.

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A number of 5‐(alkylamino)‐ or 5‐(arylamino)‐2H‐pyrrolium salts 3 or 5 have been obtained by treating the 1‐aza‐1,3‐diene hydrochlorides 2 with isocyanides R4NC in refluxing acetonitrile or chloroform for a few hours. Depending on the experimental conditions, deprotonation of these species can occur in the reaction medium to furnish the corresponding 2‐aminopyrroles 4 and 6. Insertion of isocyanide into a carbon–hydrogen bond of the pyrrolium salts can also lead to the generation of the (pyrrol‐2‐yl)methyleneiminium chlorides 7–9. Under similar conditions, treatment with an excess of tert‐butyl isocyanide converts the protonated α‐chlorocinnamaldimines 2j,k into the 5‐(tert‐butylamino)pyrrole‐2‐carbonitriles 13. Structural assignments of all the cycloadducts have been made on the basis of their NMR‐spectroscopic properties, particularly the effects observed in NOEDIFF experiments. Mechanisms are suggested to account for the ring‐closure reactions and autoxidation of pyrroles 4 and 6 under atmospheric oxygen to give the 5‐imino‐2‐pyrrolinones 17 and 18.

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“…The systematic study of the coordination chemistry of azaporphyrins had been started in our laboratory about 15 years ago [14,15], and some first results were reviewed in a monograph [16] published in Russian. Recently the influence of sequential azasubstitution on the structure of the porphyrin ligand and on its reactivity in complex formation reactions has been reviewed [17]. By the end of the last century the macrocyclic polyethers (crown ethers) had became one of the most popular chemical reagents with a very wide area of applications.…”

Section: Introductionmentioning

confidence: 99%

The synthesis and characterization of a porphyrazine bearing aza-15-crown-5 moieties in the peripheral positions and its cobalt(II) complex

Kanteki̇n

Çelenk

Bıyıklıoğlu

et al. 2007

Transition Met Chem

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Azaporphyrins: structure of the reaction centre and reactions of complex formation

Cited by 65 publications

References 59 publications

Tetrakis(selenodiazole)porphyrazines 1: Tetrakis(selenodiazole)porphyrazine and its Mg(II) and Cu(II) Derivatives. Evidence for their Conversion to Tetrakis(pyrazino)porphyrazines through Octaaminoporphyrazines

Tetrakis(selenodiazole)porphyrazines 1: Tetrakis(selenodiazole)porphyrazine and its Mg(II) and Cu(II) Derivatives. Evidence for their Conversion to Tetrakis(pyrazino)porphyrazines through Octaaminoporphyrazines

A New Access to 2-(Alkylamino)- and 2-(Arylamino)pyrroles by Addition of Isocyanides to Protonated 1-Azabutadienes

The synthesis and characterization of a porphyrazine bearing aza-15-crown-5 moieties in the peripheral positions and its cobalt(II) complex

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