Reaction cascades initiated by nucleophilic attack of heteropentalene mesomeric betaine and nitrogen-rich mesoionic tetrazolium-5-amides on electron-deficient unsaturated compounds. Synthesis of novel heterocyclic systemsElectronic supplementary information (ESI) available: synthesis of 4b; reactions of 11 and 17 with electron-deficient unsaturated compounds; alternative synthesis of 19 from 20. See http://www.rsc.org/suppdata/ob/b2/b211000h/

Araki, Shuki; Kuzuya, Masashi; Hamada, K.; Nogura, Masatoshi; Ohata, Nayumi

doi:10.1039/b211000h

Cited by 10 publications

(2 citation statements)

References 8 publications

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“…The most interesting and less examined 5-aminotetrazole derivatives are tetrazolium-5-aminides, which can be depicted as 4 by analogy with other mesoionic tetrazoles [11,12]. The first representatives of tetrazole-5-aminides were reported in the 1950s [13,14], whereas next publications were appeared only five decades later, being devoted to the synthesis and photochemistry of 1,3-diaryltetrazolium-5-aminides [15][16][17][18][19][20][21]. NMR studies of a few tetrazole-5-aminides were carried out as a part of studies of mesoionic compounds [22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

Budevich¹,

Войтехович²,

Zuraev³

et al. 2021

Beilstein J. Org. Chem.

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Tetrazolium-5-aminides have been prepared by the tert-butylation of 5-aminotetrazole and its N-methyl derivatives by the t-BuOH/HClO4 system followed by the treatment of the tetrazolium salts by alkali. The mesoionic compounds have been found to show a higher reactivity of the exocyclic N atom in comparison with 5-aminotetrazoles. The compounds reacted with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole with substitution of bromine and methylsulfonyl groups giving the corresponding tetrazolium salts or conjugate aminides. The obtained mesoionic tetrazoles have been characterized by elemental analysis, FTIR, NMR, and UV–vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, its N,N’-ethylene-bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. The structural and spectral features of the tetrazolium-5-aminides are discussed by using quantum-chemical calculations.

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Section: Introductionmentioning

confidence: 99%

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

Budevich¹,

Войтехович²,

Zuraev³

et al. 2021

Beilstein J. Org. Chem.

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show abstract

“…The most interesting and less examined 5-aminotetrazole derivatives are tetrazolium-5-aminides, which can be depicted as 4 by analogy with other mesoionic tetrazoles [11,12]. The first representatives of tetrazole-5-aminides were reported in the 1950s [13,14], whereas next publications were appeared only five decades later, being devoted to synthesis and photochemistry of 1,3-diaryltetrazolium-5-aminides [15][16][17][18][19][20][21]. NMR studies of few tetrazole-5-aminides were carried out as a part of studies of mesoionic compounds [22][23][24].…”

mentioning

confidence: 99%

Mesoionic tetrazolium-5-aminides: Synthesis, Molecular and Crystal Structures, UV-Vis Spectra, and DFT Calculations

Budevich¹,

Войтехович²,

Zuraev³

et al. 2020

Preprint

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Tetrazolium-5-aminides have been prepared by tert-butylation of 5-aminotetrazole and its N-methyl derivatives by t-BuOH/HClO4 system followed by treatment of tetrazolium salts by alkali. These mesoionic compounds have been found to show higher reactivity of exocyclic N atom in comparison with 5-aminotetrazoles. They react with 1,2-dibromoethane and 5-(methylsulfonyl)-1-phenyl-1H-tetrazole and substitute bromine and methylsulfonyl groups giving tetrazolium salts or conjugate aminides. Obtained mesoionic tetrazoles have been characterized by elemental analysis, FT-IR, NMR and UV-Vis spectroscopy, TGA/DSC analysis and for 1,3-di-tert-butyltetrazolium-5-aminide, it’s N,N’-ethylene bridged bis-derivative and (1,3-di-tert-butyl-1H-tetrazol-3-ium-5-yl)(1-phenyl-1H-tetrazol-5-yl)amide by single crystal X-ray analysis. Structural and spectral features of tetrazolium-5-aminides are discussed by using quantum-chemical calculations.

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Mesoionic carbenes: Reactions of 1,3‐diphenyltetrazol‐5‐ylidene with electron‐deficient alkenes, and synthesis and catalytic activities of the (tetrazol‐5‐ylidene)rhodium(I) complexes

Araki

Yokoi

Sato

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).The reactions of 1,3-diphenyltetrazol-5-ylidene, a rare example of mesoionic carbenes, with electrondeficient unsaturated compounds were studied. The carbene reacted with dimethyl 1,2,4,5-tetrazine-3, 6-dicarboxylate to give a 5-tetrazoliomethylide, together with hydrazine derivatives. The reaction with tetracyanoethylene gave another methylide in low yield. On the contrary, the reactions with weaker electrophiles, such as 3,6-diphenyl-1,2,4,5-tetrazine, fumalonitrile, N-phenylmaleimide, and dimethyl acetylenedicarboxylate, did not give any coupling products, but gave phenylated products and/or Michael addition products via the degradation of the 1,3-diphenyltetrazole ring. Novel mesoionic monoand bis(carbene)-rhodium(I) complexes were synthesized and the structures were characterized by X-ray crystallography. Their catalytic activities for the decarbonylative addition reaction of benzoyl chloride to ethynylbenzene were investigated.

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Cited by 10 publications

References 8 publications

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

Mesoionic tetrazolium-5-aminides: Synthesis, Molecular and Crystal Structures, UV-Vis Spectra, and DFT Calculations

Mesoionic carbenes: Reactions of 1,3‐diphenyltetrazol‐5‐ylidene with electron‐deficient alkenes, and synthesis and catalytic activities of the (tetrazol‐5‐ylidene)rhodium(I) complexes

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