A New Synthesis of 1,2-Diazetines via Simple Cycloacylation Reactions

Pufky, Daniela; Beckert, Rainer; Döring, Manfred; Walter, Olaf

doi:10.3987/com-02-9490

HETEROCYCLES

2002

DOI: 10.3987/com-02-9490

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A New Synthesis of 1,2-Diazetines via Simple Cycloacylation Reactions

Daniela Pufky¹,

Rainer Beckert²,

Manfred Döring³

et al.

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Cited by 10 publications

References 4 publications

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From Byproducts to Efficient Fluorophores: A Route to the Synthesis of Fluorubines

Fleischhauer¹,

Beckert²,

Jüttke³

et al. 2009

Chemistry A European J

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The reaction of bis(imidoyl) chlorides of oxalic acid with monoalkyl hydrazines leads to substituted Delta(2)-1,2-diazetines, which are versatile building blocks for ring-transformation reactions. One remarkable product originating from side reactions featured by a strong orange/red fluorescence was confirmed as a novel fluorubine derivative. In continuing our studies to substituted oligoazaacenes, we developed several synthetic entries to build up novel fluorubine derivatives, in which particularly aminobridged bis(quinoxaline)s are the key products for cationic hexaazapentacenes. We would like to discuss the possible formation pathways of these fluorubine derivatives, which exhibit interesting photophysical and chemical properties. The structures of all new derivatives were confirmed by common analytical methods (NMR spectroscopy, CV, UV/Vis, mass spectrometry, elemental analysis, and X-ray structural analysis) and will be discussed on selected examples in more detail.

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From Byproducts to Efficient Fluorophores: A Route to the Synthesis of Fluorubines

Fleischhauer¹,

Beckert²,

Jüttke³

et al. 2009

Chemistry A European J

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View full text Add to dashboard Cite

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A New Synthesis of 1,2‐Diazetines via Simple Cycloacylation Reactions.

et al. 2002

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A New Synthesis of Push‐Pull Pyrroles, Their Oxidation to Stable 3H‐Pyrroles and an Unexpected Anellation Reaction

et al. 2009

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A new synthesis of push-pull pyrroles of type 5 was developed starting from bis(imidoyl chlorides) 1 and various iminodiacetic acid derivatives 3. The use of appropriate N-trifluoroacetyl residues as protecting/activating group proved to be the method of choice for the straightforward preparation of the 3,4-diarylamino-1H-pyrroles 5. When benzothiazole substructures are present in 2,5-position of heterocycles 5, a two-

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A New Synthesis of 1,2-Diazetines via Simple Cycloacylation Reactions

Cited by 10 publications

References 4 publications

From Byproducts to Efficient Fluorophores: A Route to the Synthesis of Fluorubines

From Byproducts to Efficient Fluorophores: A Route to the Synthesis of Fluorubines

A New Synthesis of 1,2‐Diazetines via Simple Cycloacylation Reactions.

A New Synthesis of Push‐Pull Pyrroles, Their Oxidation to Stable 3H‐Pyrroles and an Unexpected Anellation Reaction

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