Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes

Becher, Jan; Joergensen, Per Lauge; Pluta, Krystian; Krake, Niels; Fält-Hansen, Birgitte

doi:10.1021/jo00033a039

Cited by 47 publications

(18 citation statements)

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“…[ An analogous transformation of nitrene 286, generated from the azide 285, is a key step in the nucleophilic telesubstitution [130] of 2-chloro-1-methylindole-3-carbaldehyde (284) with azide anion, resulting in the formation of 5-azido-1-methylindole-3-carbonitrile (290) via 287Ϫ289 (Scheme 66). [131,132] Conclusions Aza-ortho-xylylenes have become intermediates of potential application in organic synthesis. The arsenal of methods used for the generation of these reactive intermediates is broadening.…”

Section: Aza-ortho-xylylenes By Ring Opening Of Heterocyclic Systemsmentioning

confidence: 99%

Aza-ortho-xylylenes in Organic Synthesis

Wojciechowski

2001

Eur. J. Org. Chem.

126

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Section: Aza-ortho-xylylenes By Ring Opening Of Heterocyclic Systemsmentioning

confidence: 99%

Aza-ortho-xylylenes in Organic Synthesis

Wojciechowski

2001

Eur. J. Org. Chem.

126

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“…So compound 2 is used in the synthesis of new compound 4 through four indirect processes involving preparation of other new compounds 3, 5, 6, and 7.The first process involved treating of compound 2 with sodium azide using dimethylformamide as a solvent to afford the tetrazolo [1,5-g] [1,4]benzodiazepines 3. The formation of compound 3 is suggested to proceed via intramolecular azide cycloaddition reaction [16][17][18][19][20][21] (Scheme 1). The structure of compound 3 was confirmed by elemental and spectroscopic analysis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Azab

2013

Journal of Heterocyclic Chem

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Preparation of 4‐chloro‐3H‐benzo[b][1,4]diazepine‐2‐carbaldehyde 5, which is used as a key intermediate in the synthesis of chalcones derivatives, via its condensation with some aromatic acetophenone derivatives under ethanol piperidine condition was described. Also illustrated was the reaction of such chalcones with available nucleophilics and reagents of active methylene group to afford new series of fused and isolated pyrazoles, isoxazolines pyrimidines, pyridines, triazolo[1,5‐a]pyrimidines, benzo[1,4]oxa(thia)zepines, and pyrido[1,2‐a]benzimidazoles incorporating 4‐chloro‐3H‐benzo[b][1,4]diazepine moiety, which have a potential pharmaceutical interest. Furthermore, condensation reaction of 4‐chloro‐3H‐benzo[b][1,4]diazepine‐2‐carbaldehyde with aromatic amine derivatives to afford the Schiff's bases was described. The C═N double bond of the latter compounds has been reacted with chloroketene to give β‐lactams and with sulfanylacetic acid to give the 2‐(4‐oxo‐1,3‐thiazolidinyl)‐substituted derivative. The structures of the newly prepared compounds were established by elemental analysis, IR, MS, and 1H NMR spectral analysis.

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“…In the HMBC spectrum of VIII, protons of the N-methyl group showed the only cross peak with a carbon atom whose signal is located at C 159.27 ppm. According to published data [11], this signal belongs to the carbon atom attached to the hydroxy group (the CNO 2 carbon atom gives a broadened signal at C 150.46 ppm). Thus the COH carbon atom is closer to the NCH 3 group than CNO 2 , i.e., intramolecular substitution of nitro group in compound VI occurs just at position 5.…”

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confidence: 80%

Nitropyrazoles: XII. Transformations of the 4-Methyl Group in 1,4-Dimethyl-3,5-dinitropyrazole and Cyclization of the Transformation Products

et al. 2005

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A preparative procedure for the synthesis of 1,4-dimethyl-3,5-dinitropyrazole by nitration of 1,4-dimethylpyrazole was developed. The reaction of 1,4-dimethyl-3,5-dinitropyrazole with dimethoxymethyl-(dimethyl)amine (N,N-dimethylformamide dimethyl acetal) gave (E)-N,N-dimethyl-2-(1-methyl-3,5-dinitropyrazol-4-yl)ethenylamine. Acid hydrolysis of the latter afforded (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde, and the reaction with sodium nitrite in hydrochloric acid led to formation of 2-hydroxymino-2-(1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde. The corresponding O-methyloxime and phenylhydrazone reacted with K 2 CO 3 to give 6-methyl-4-nitropyrazolo[4,3-d]isoxazole-3-carbaldehyde O-methyloxime and 1-methyl-3-nitro-4-(2-phenyl-2H-1,2,3-triazol-4-yl)pyrazol-5-ol, respectively. Treatment of (1-methyl-3,5-dinitropyrazol-4-yl)-acetaldehyde with benzenediazonium chloride gave (1-methyl-3,5-dinitropyrazol-4-yl)acetaldehyde phenylhydrazone which underwent intramolecular cyclization with replacement of the 5-nitro group by the action of K 2 CO 3 in acetonitrile; in the reaction with K 2 CO 3 in ethanol, the 5-nitro group was replaced by ethoxy.* For communication XI, see [1].

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Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes

Cited by 47 publications

References 0 publications

Aza-ortho-xylylenes in Organic Synthesis

Aza-ortho-xylylenes in Organic Synthesis

Synthesis of Some New Benzo[b][1,4]diazepine Based Heterocycles

Nitropyrazoles: XII. Transformations of the 4-Methyl Group in 1,4-Dimethyl-3,5-dinitropyrazole and Cyclization of the Transformation Products

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