Benzisoxazol

Benzisoxazol
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Nome IUPAC 1,2-Benzisoxazole
Outros nomes 2,1-Benzisoxazol, Antranil, Benzo[d]isoxazol, Benz[c]isoxazol
Identificadores
Número CAS 271-58-9
PubChem 67498
Número EINECS 205-980-5
ChemSpider 64227
ChEBI 51554
SMILES
InChI
1/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H
Propriedades
Fórmula química C7H5NO
Massa molar 119.12 g mol-1
Aparência Líquido incolor
Densidade 1.18 g/cm3
Ponto de ebulição

35-38°C (2.67 hPa)
101-102 °C (2 kPa)

Riscos associados
Frases S S24/25, S28A, S37, S45
Página de dados suplementares
Estrutura e propriedades n, εr, etc.
Dados termodinâmicos Phase behaviour
Solid, liquid, gas
Dados espectrais UV, IV, RMN, EM
Exceto onde denotado, os dados referem-se a
materiais sob condições normais de temperatura e pressão
Referências e avisos gerais sobre esta caixa.
Alerta sobre risco à saúde.

Benzisoxazol, ou antranil, é um composto orgânico aromático heterocíclico com fórmula molecular C7H5NO contendo um anel benzeno fundido a uma estrutura em anel isoxazol.[1][2] Benzisoxazol não tem uso doméstico, sendo usado principalmente na indústria e pesquisa.

Sendo um composto heterocíclico, benzisoxazol encontra uso em pesquisa como um material de partida para a síntese de maiores estruturas, usualmente bioativas. É encontrado dentro de estruturas químicas de fármacos, tais como o antipsicótico risperidona e o anticonvulsivante zonisamida.[3][4][5]

Sua aromaticidade o faz relativamente estável, embora, como um heterocíclico, tenha sítios reativos que permitam a funcionalização.[6]

Síntese

Vários benzisoxazóis substituídos têm sido preparados por um cicloadição de óxidos de nitrilo e arinas. Ambos os intermediários são altamente reativos, e gerados in situ por ânion fluoreto a partir de precursores arina facilmente preparados e cloro-oximas.[7][8]

Uma síntese divergente e regiosseletiva quer de benzisoxazóis 3-substituídos ou benzisoxazóis 2-substituídos facilmente acessível a partir de orto-hidroxiarilo NH-cetiminas prossegue em duas vias distintas através de uma imina N-Cl intermediária comum com duas rotas sintéticas: com não formação de ligação para formar benzisoxazol sob condições anidras e reação do tipo rearranjo de Beckmann mediada por hipoclorito de sódio para formar benzisoxazol, respectivamente.[8][9][10]

Brometo de ferro(II) catalisa a transformação de aril e vinil azidas com substituintes cetona ou metil oxima em 2,1-benzisoxazóis, indazóis ou pirazóis através da formação de ligações N-O ou N-N. Esta transformação tolera vários grupos funcionais e facilita o acesso a uma variedade de benzisoxazóis ou indazóis.[8][11]

Referências

  1. ↑ Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry 2nd ed. [S.l.]: Academic Press. ISBN 0080429882 
  2. ↑ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6 
  3. ↑ Yin Chen, et al; Synthesis and evaluation of amide, sulfonamide and urea – benzisoxazole derivatives as potential atypical antipsychotics; Med. Chem. Commun., 2015,6, 831-838; DOI: 10.1039/C4MD00578C
  4. ↑ Anabella Villalobos, et al; Novel Benzisoxazole Derivatives as Potent and Selective Inhibitors of Acetylcholinesterase; J. Med. Chem., 1994, 37 (17), pp 2721–2734; DOI: 10.1021/jm00043a012
  5. ↑ M. Shimizu, et al; 1,2-Benzisoxazole-3-acetamidoxime hydrochloride, a new psychotropic agent; Experientia, 15. 4. 1974, Volume 30, Issue 4, p 405; DOI 10.1007/BF01921689
  6. ↑ PVV Satyanarayana; Chapter-2 - Synthesis of 2-substituted benzoxazole, benzimidazole and benzothiazole derivatives; 2015. - shodhganga.inflibnet.ac.in
  7. ↑ Anton V. Dubrovskiy and Richard C. Larock; Synthesis of Benzisoxazoles by the [3 + 2] Cycloaddition of in situ Generated Nitrile Oxides and Arynes; Org. Lett., 2010, 12, 1180-1183. DOI: 10.1021/ol902921s
  8. ↑ a b c Synthesis of benzisoxazoles - www.organic-chemistry.org
  9. ↑ Cheng-yi Chen , Teresa Andreani, and Hongmei Li; A Divergent and Selective Synthesis of Isomeric Benzoxazoles from a Single N–Cl Imine; Org. Lett., 2011, 13 (23), pp 6300–6303; DOI: 10.1021/ol202844c
  10. ↑ Ramesh Dhani; BENZOXAZOLE: THE MOLECULE OF DIVERSE PHARMACOLOGICAL ACTIVITIES - www.pharmaresearchlibrary.com
  11. ↑ Benjamin J. Stokes, Carl V. Vogel, Linda K. Urnezis, Minjie Pan and Tom G. Driver; Intramolecular Fe(II)-Catalyzed N-O or N-N Bond Formation from Aryl Azides; Org. Lett., 2010, 12, 2884-2887. DOI: 10.1021/ol101040p

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