2004
DOI: 10.1016/j.tet.2004.04.067
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Synthesis of mesoionic[1,2,3]triazolo[5,1-d][1,2,5]triazepines

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Cited by 16 publications
(10 citation statements)
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“…Methylation and benzylation of products 1158 occurs selectively on the triazole N-3 atom giving rise to mesoionic systems 1159 ( Scheme 191 ) <2002J(P1)211> . Under similar reaction conditions, dihydrazide 1160 is converted to triazole 1163 via intermediate diazo derivative 1161 ( Scheme 192 ) <2004T5367> . Resonance form 1162 and others with definitely positive charge on the diazo nitrogen atoms seem to be responsible for the cyclization.…”
Section: Ring Synthesis From Acyclic Compoundsmentioning
confidence: 99%
“…Methylation and benzylation of products 1158 occurs selectively on the triazole N-3 atom giving rise to mesoionic systems 1159 ( Scheme 191 ) <2002J(P1)211> . Under similar reaction conditions, dihydrazide 1160 is converted to triazole 1163 via intermediate diazo derivative 1161 ( Scheme 192 ) <2004T5367> . Resonance form 1162 and others with definitely positive charge on the diazo nitrogen atoms seem to be responsible for the cyclization.…”
Section: Ring Synthesis From Acyclic Compoundsmentioning
confidence: 99%
“…Likewise, fused triazepine derivatives with a bridgehead nitrogen atom in the molecule exhibit interesting biological properties [22]. Various conventional methods for the synthesis of fused triazepines are exempli�ed in the literature [23,24] using cycloaddition [25] and photochemical methods, but pyrimido[3 � ,2 � :4,5]thieno [3,2:4,5]pyrimido [1,6-b] [1,2,4]triazepines are the least investigated group among the fused triazepines. Moreover, no general method is ever reported for the synthesis of the title compounds starting from 7amino-8-imino-pyrimido [3,2:4,5]thieno [2,3-d]pyrimidine (10).…”
Section: Introductionmentioning
confidence: 99%
“…Some condensed mesoionic 1,2,3-triazolium-5-olates have been shown to act as immunosuppressants [9]. Previously we have shown [10][11][12] that alkylation of 1-aryl-and 1-arylmethyleneamino-1,2,3-triazol-5-olate sodium salts with alkyl halides leads to the zwitterionic 3-alkyl-1,2,3-triazol-3-ium-5-olate and [1,2,3]triazolo[1,5-а]pyrazinium-3-olate. In a continuation of our research in the field of mesoionic heterocycles [13][14][15][16], in this work we present the synthesis of new [1,2,3]triazolo[1,5-a]pyrazinium-3-olate derivatives.…”
mentioning
confidence: 96%
“…The geometry of 3-phenacyl-and 3-cyanomethyl derivatives of triazolium-5-olates 1а-с [10][11][12] indicates a possible interaction of carboxamide group nitrogen atom at position 4 of the triazole ring with keto or cyano groups, forming a condensed zwitterionic triazolopyrazine. Indeed, refluxing of 3-cyanomethyl derivatives 1a-c with sodium ethoxide for 5 h resulted in good yields (up to 80%) of the individual bicyclic compounds 2a-c.…”
mentioning
confidence: 99%