XXXIV.—2 : 5-Iminodihydro-1 : 2 : 3-triazole. Part I. Constitution of Dimroth's 5-anilinotriazole

Dutt, Pavitra Kumar

doi:10.1039/ct9232300265

Cited by 6 publications

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“…Alternatively, with another functional group placed on the chain bonded in position 1, the scaffold can be modeled according to the turn required and/or the reagents employed. Nevertheless, although known since the beginning of the 20th century, the 5-amino-1,2,3-triazole 4 carboxylates have found relatively few applications …”

Section: Introductionmentioning

confidence: 99%

Ruthenium-Catalyzed Synthesis of 5-Amino-1,2,3-triazole-4-carboxylates for Triazole-Based Scaffolds: Beyond the Dimroth Rearrangement

et al. 2015

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The 5-amino-1,2,3-triazole-4-carboxylic acid is a suitable molecule for the preparation of collections of peptidomimetics or biologically active compounds based on the triazole scaffold. However, its chemistry may be influenced by the possibility of undergoing the Dimroth rearrangement. To overcome this problem, a protocol based on the ruthenium-catalyzed cycloaddition of N-Boc ynamides with azides has been developed to give a protected version of this triazole amino acid. When aryl or alkyl azides are reacted with N-Boc-aminopropiolates or arylynamides, the cycloaddition occurs with complete regiocontrol, while N-Boc-alkyl ynamides yield a mixture of regioisomers. The prepared amino acids were employed for the preparation of triazole-containing dipeptides having the structural motives typical of turn inducers. In addition, triazoles active as HSP90 inhibitors (as compound 41, IC50 = 29 nM) were synthesized.

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Section: Introductionmentioning

confidence: 99%

Ruthenium-Catalyzed Synthesis of 5-Amino-1,2,3-triazole-4-carboxylates for Triazole-Based Scaffolds: Beyond the Dimroth Rearrangement

et al. 2015

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Bridged 3/4 Through 5/6 Ring Systems

1961

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Die Thermolyse des Phenylazids in primären Aminen; die Konstitution des Dibenzamils

1958

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Das von L. Wolff beim Zerfall des Phenylazids in Anilin erhaltene „Dibenzamil”︁ erweist sich als ungesättigtes Amidin mit siebengliedrigem Ring (IV oder V). Auch analoge Produkte aus Phenylazid und p‐Toluidin, p‐Phenetidin, N‐Methyl‐anilin, Benzylamin oder Cyclohexylamin sowie aus p‐Tolylazid und Anilin werden beschrieben. Ihre Konstitution zeigt, daß das zerfallende Arylazid den siebengliedrigen Ring bildet und das Arylamin in die Seitenkette eingeht. Die Acylierung von IV, nicht aber die Benzolsulfonylierung, ist mit einer Rückehr in die Benzolreihe verbunden.

show abstract

XXXIV.—2 : 5-Iminodihydro-1 : 2 : 3-triazole. Part I. Constitution of Dimroth's 5-anilinotriazole

Cited by 6 publications

References 0 publications

Ruthenium-Catalyzed Synthesis of 5-Amino-1,2,3-triazole-4-carboxylates for Triazole-Based Scaffolds: Beyond the Dimroth Rearrangement

Ruthenium-Catalyzed Synthesis of 5-Amino-1,2,3-triazole-4-carboxylates for Triazole-Based Scaffolds: Beyond the Dimroth Rearrangement

Bridged 3/4 Through 5/6 Ring Systems

Die Thermolyse des Phenylazids in primären Aminen; die Konstitution des Dibenzamils

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