Studies with 2‐arylhydrazononitriles: A novel simple, efficient route to 5‐acyl‐2‐substituted‐1,2,3‐triazol‐4‐amines

Aziz, Suzan Ibrahim; Anwar, Hany F.; Elnagdi, Mohamed Hilmy; Fleita, Daisy H.

doi:10.1002/jhet.5570440335

Cited by 11 publications

(6 citation statements)

References 22 publications

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“…Coupling of the key intermediate 8 with 3-chlorobenzenediazonium chloride 10 was expected to afford the desired product 1 . 8,9 Cyanomethyl derivative 8 could be formed from ethyl ester 6 . 10 Isoxazole 6 would be derived from the commercially available pinacolone 2 and oxalic acid diethyl ester 3 .…”

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confidence: 99%

Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist

Chen

Ding

Wild

et al. 2013

Tetrahedron Letters

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A concise and efficient synthetic approach to producing a novel non-cyclic nucleotide EPAC antagonist ESI-09 and its new analogs is reported. Key features of the synthesis include a mild and reliable one-pot procedure for an isoxazole synthon, as well as a modified one-pot protocol for the cyanomethyl ketone key intermediate. The synthesis requires inexpensive starting materials and only three linear steps for the completion in a total yield of 53%.

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confidence: 99%

Efficient synthesis of ESI-09, a novel non-cyclic nucleotide EPAC antagonist

Chen

Ding

Wild

et al. 2013

Tetrahedron Letters

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“…Another transformation of bis(hydrazones), hydrazonoamidoximes, and hydrazonohydrazides yielding 2-aryl-1,2,3-triazoles usually occurs under condensation conditions and is accomplished by the elimination of a leaving group [240,[275][276][277][278][279][280][281][282][283][284][285][286][287][288][289][290][291][292][293][294].…”

Section: Intramolecular Cyclization Of Bis(hydrazones) and Hydrazonoamentioning

confidence: 99%

“…Cyclization of arylhydrazone oximes 223 by dehydration agents (Ac 2 O, SOCl 2 , hydroxylamine-O-sulfonic acid) led to 2-aryl-1,2,3-triazoles in the same manner (Scheme 78) [282][283][284][285][286][287][288][289][290].…”

Section: Intramolecular Cyclization Of Bis(hydrazones) and Hydrazonoamentioning

confidence: 99%

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Chemistry of 1,2,3-triazoles

Dehaen¹

2015

Topics in Heterocyclic Chemistry

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The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community.The series consists of topic related volumes edited by renowned editors with contributions of experts in the field.More information about this series at

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“…β -Oxoalkanonitriles are versatile reagents and their chemistry has received in the past [ 1 ] and continues to receive considerable attention [ 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 ]. In conjunction with our interest in utilizing oxoalkanonitriles to prepare azolylazines [ 10 , 11 , 12 , 13 ] a route to 3-(4-pyridyl)-3-oxopropanenitrile was needed. 4-Pyridyl derivatives possess many pharmacological activities [ 14 ], and they can also be used as N -donor ligands in complexation with metal ions with superior cytotoxicity towards bacteria [ 15 ].…”

Section: Introductionmentioning

confidence: 99%