2005
DOI: 10.1002/hc.20061
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New benzylpiperazine derivatives bearing mono‐ and bis‐dialkyl substituted 1,2,4‐triazoles

Abstract: Cycloaddition of the 1‐aza‐2‐azoniaallenes 3 with p‐cyanobenzyl chlorides afforded, after spontaneous rearrangement, the 1,5‐dialkyl‐3‐[4‐chloromethyl)phenyl]‐1H‐[1,2,4]‐triazoles 6. A series of 1,5‐dialkyl‐1H‐[1,2,4]‐triazol‐3‐yl)benzyl‐piperazines 7 and 8 were prepared from direct condensation of 6 with piperazine and N‐methylpiperazine, respectively. The structures of the newly synthesized products were identified by 2D NMR spectroscopy. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:28–32, 2005; Publish… Show more

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Cited by 11 publications
(4 citation statements)
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“…[16] Alternatively, α,α -dichloroazo compounds e, prepared by chlorination of azines d, [17] have been used in preparation of the 1-aza-2-azoniallene salts with a more suitable leaving group (CClR 3 R 4 ) f ( Figure 1). This method included spontaneous rearrangements: the [1,2]-tert-butyl group migration followed by elimination processes.…”
Section: Resultsmentioning
confidence: 99%
“…[16] Alternatively, α,α -dichloroazo compounds e, prepared by chlorination of azines d, [17] have been used in preparation of the 1-aza-2-azoniallene salts with a more suitable leaving group (CClR 3 R 4 ) f ( Figure 1). This method included spontaneous rearrangements: the [1,2]-tert-butyl group migration followed by elimination processes.…”
Section: Resultsmentioning
confidence: 99%
“…Literature has reported that 1,3-dipolar cycloaddition as one type of pericyclic reactions relating to six electrons could perform a versatile and efficient one-pot reaction to access five-membered heterocycles [84][85][86][87][88][89] particularly triazole derivatives starting from available oximes, hydrazones and hydrazonoyl halides [90][91][92]. The 1,3-dipolar cycloaddition of phenyl substituted hydrazonoyl chloride 59 with oxime 60 in the presence of excess triethylamine could generate triazole derivative 61 with broad antimicrobial spectrum (Scheme 22).…”
Section: Other Hydrazonesmentioning
confidence: 99%
“…In addition, it was mentioned that [1,3,4]thiadiazoles exhibited various biological activities possibly due to the presence of the =N-C-S moiety [16]. In connection with our strategy in the synthesis of new amino acid derivatives [17][18][19], we report here the synthesis of new 1,2,4-triazolo-naphthalene and thiadiazole derivatives derived from amino acid analogues, and the evaluation of their anti-HIV activity.…”
Section: Introductionmentioning
confidence: 96%