Ringtransformationen von Pyrazolinonen �ber Azoolefine - ein neuer Zugang zum 1,2,3-Thiadiazol-System

Lutze, G.; Kirschke, Klaus; Hübner, Petra; Schmitz, Ernst; Ramm, M.; Krauß, Norbert

doi:10.1002/prac.19933350209

Cited by 6 publications

References 6 publications

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Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives

2001

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Keywords: Ring opening / Isomerizations / Cyclizations / Heteroaromaticity / RearrangementsRing transformations of five-membered heterocycles and their benzologues for the recent 10 years are discussed and reviewed. These transformations are classified into four groups: (a) ''classical ring transformations'', where the starting and resulting ring system is of the same size, but the heteroatoms and/or their positions have been changed; (b) ''degenerate ring transformations'', where during the course of the transformation the starting compound and product have the same ring system, but the reaction proceeds by a A. IntroductionRearrangements of heterocyclic rings by temporary opening and subsequent closure to a new molecule are of par- [a] (1993). His research interests are mainly devoted to heterocyclic chemistry, synthesis and application of isotopically labelled compounds and, more recently, macrocyclic ring systems with regard to host-guest chemistry.MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included.

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Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives

2001

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ChemInform Abstract: Ring Transformations of Pyrazolinones via Azoolefins ‐ A New Way to the 1,2,3‐Thiadiazol System.

et al. 1994

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1-Arylimino-pyrazol-Betaine, Pyrazole und 1,2,4-Triazine aus 3-Arylazo-propens�ure-N-chloroamiden

Lutze¹,

Kirschke²,

Krauß

1993

J. Prakt. Chem.

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1‐Arylimino‐pyrazole Betaines, Pyrazoles and 1,2,4‐Triazines from 3‐Arylazo‐propenoic Acid N‐Chloramides Reaction of 3‐arylazo‐propenoic acid amides 5 with NaOCl yields N‐chloroamides 6 which give under alkaline conditions 1,2,4‐triazines 9 and 10 (products of a Hofmann degradation). This reaction competes with an intramolecular electrophilic amination and a 1,2‐shift reaction giving 1‐arylimino‐pyrazole betaines 11 and 4‐chloroimino‐pyrazolones 13. Exchange of the halogen in 11 with nucleophiles leads to further betaines 12. Bis‐pyrazole 14 and 1,2,3‐triazoles 15 are available from 13b. The X‐ray structure analysis of compound 11b is discussed.

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Ringtransformationen von Pyrazolinonen �ber Azoolefine - ein neuer Zugang zum 1,2,3-Thiadiazol-System

Cited by 6 publications

References 6 publications

Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives

Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives

ChemInform Abstract: Ring Transformations of Pyrazolinones via Azoolefins ‐ A New Way to the 1,2,3‐Thiadiazol System.

1-Arylimino-pyrazol-Betaine, Pyrazole und 1,2,4-Triazine aus 3-Arylazo-propens�ure-N-chloroamiden

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