Gas-phase thermolysis of benzotriazole derivatives. Part 3: Kinetic and mechanistic evidence for biradical intermediates in pyrolysis of aroylbenzotriazoles and related compounds

Al‐Awadi, Nouria A.; George, Bobby J.; Dib, Hicham H.; Ibrahim, Maher R.; Ibrahim, Yehia A.; El‐Dusouqui, Osman M. E.

doi:10.1016/j.tet.2005.06.028

Cited by 53 publications

(19 citation statements)

References 39 publications

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“…The pyrolysis of a number of 1-aroylbenzotriazoles 180 under different conditions gave the corresponding benzoxazole derivatives 181 in 13-18% yields alongside with other products 182-186, depending on the nature of the substituents on the acyl moiety (Scheme 39) [66]. …”

Section: Oxazoles and Oxazolidinesmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

Bol’shakov

2015

Topics in Heterocyclic Chemistry

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This review aims at delivering an overview of the synthetic utility of benzotriazole and its derivatives for the preparation of oxygen-containing heterocycles. This review serves both as a synthetic guide and as a theoretical handbook of benzotriazole-assisted preparations of oxygen heterocycles and offers a complete overview of existing applications for benzotriazole and its derivatives in heterocyclic synthesis. Multiple examples reveal the superiority of benzotriazole-based approaches over conventional ones.

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Section: Oxazoles and Oxazolidinesmentioning

confidence: 99%

Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

Bol’shakov

2015

Topics in Heterocyclic Chemistry

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“…22 Além destes métodos, as fenantridinonas (1) podem ser obtidas pelo rearranjo térmico de 2-alcoxifenantridinas 23 ou cicloadições de Diels-Alder, 24 ou, fotoquimicamente, por irradiação de aril-hidrazonas de benzotriazol (Figura 2, B), 25 ou por foto-desidro--halogenação de benzoilanilinas (Figura 2, C), [26][27][28] foto-ciclo-adição de estirenos com isoquinolinonas, 29 ou por pirólise de derivados de 3-arilidenoamino-1,2,3-benzotriazin-4-onas 30 e de benzoilbenzotriazóis (Figura 2, B). 31 Outros métodos envolvendo intermediários radicalares incluem a reação de Pschorr 32 e ciclizações promovidas por reagentes como Bu 3 SnH, 33 SmI 2 /HMPA 34 ou TTMSS 35 na presença de oxigênio (Figura 2, C). O mecanismo destas reações radicalares passa por um intermediário, um espirocicloexadieniloxindol, que pode, ou não, sofrer um rearranjo para gerar 1 dependendo das condições reacionais.…”

Section: Introductionunclassified

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Costa¹,

Silva²,

Lucas³

et al. 2016

Química Nova

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publicado na web em 18/02/2015 SYNTHESIS OF PHENANTHRIDINONE DERIVATIVES BY DIRECT ARYLATION. CHARACTERIZATION OF THE ABSORPTION AND EMISSION SPECTRA FOR REPRESENTATIVE EXAMPLES. The phenanthridinone heterocyclic system has attracted considerable attention in recent years due to the diverse array of physical, chemical and pharmacological properties demonstrated by natural and synthetic derivatives. As a consequence there has been considerable development of synthetic methodology for the synthesis of this and related heterocyclic ring systems. The synthetic literature is discussed and is compared with a direct arylation methodology for the intramolecular cyclization of tertiary (2-iodo)benzoylamides to generate the biaryl bond of these compounds. The efficient methodology allowed the synthesis of a number of previously unknown phenanthridinone products. The photoluminescent properties of representative examples were characterized and it is proposed that the previously unknown compound 1s reveals dual fluorescence in a manner similar to the known compound 1r.

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“…Gas‐phase pyrolysis provides a useful alternative synthetic strategy for the preparation of novel condensed heterocycles. Many valuable heterocyclic compounds of synthetic importance and potential biological, pharmaceutical, and industrial applications have been prepared using the two major gas‐phase pyrolysis methodologies: static (sealed‐tube) pyrolysis (STP) and flash vacuum pyrolysis (FVP) . Both processes are conducted at low pressure, while FVP is further characterized by relatively short (millisecond) substrate residence time .…”

Section: Introductionmentioning

confidence: 99%

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]

Al-Awadi

Ibrahim

El‐Dusouqui

et al. 2014

J. Heterocyclic Chem.

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in Wiley Online Library (wileyonlinelibrary.com).Gas-phase pyrolysis of N-arylidine-N′-pyrimidin-2-yl-hydrazine derivatives 1a-e gave the corresponding arylnitriles 2a-e, 2-aminopyrimidine 3, 3-phenyl-1,2,4-triazolo[4,3-a]pyrimidines 4, 2-phenyl-1,2,4-triazolo [1,5-a]pyrimidines 5, 2,4,5-triphenyl-1H-imidazole 6, and 2,3-diphenylquinoline 7. The analyses of the reaction products are reported and used to elucidate the mechanism of the pyrolytic process.

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Gas-phase thermolysis of benzotriazole derivatives. Part 3: Kinetic and mechanistic evidence for biradical intermediates in pyrolysis of aroylbenzotriazoles and related compounds

Cited by 53 publications

References 39 publications

Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

Benzotriazole-Mediated Synthesis of Oxygen-Containing Heterocycles

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Product and Mechanism of Gas-phase Pyrolysis of 2-arylidinehydrazinopyrimidines: Interesting Route to Condensed Heterocycles[1]

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