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Catalyst-Controlled Structural Divergence: Selective Intramolecular 7-endo-dig and 6-exo-dig Post-Ugi Cyclization for the Synthesis of Benzoxazepinones and Benzoxazinones.
Singh, Karandeep; Malviya, Bhanwar Kumar; Roy, Tapta Kanchan; Mithu, Venus Singh; Bhardwaj, Vimal K; Verma, Ved Prakash; Chimni, Swapandeep Singh; Sharma, Siddharth.
Afiliación
  • Singh K; Department of Chemistry, Mohanlal Sukhadia University , Udaipur 313001, India.
  • Malviya BK; Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University , Amritsar 143005, India.
  • Roy TK; Department of Chemistry, Mohanlal Sukhadia University , Udaipur 313001, India.
  • Mithu VS; Department of Chemistry and Chemical Sciences, Central University of Jammu , Jammu 180011, India.
  • Bhardwaj VK; Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University , Amritsar 143005, India.
  • Verma VP; Department of Chemistry, Indian Institute of Technology Ropar (IIT Ropar) , Rupnagar 140001, India.
  • Chimni SS; Department of Chemistry, Banasthali University , Newai-Jodhpuriya Road, Vanasthali 304022, India.
  • Sharma S; Department of Chemistry, U.G.C. Centre of Advance Studies in Chemistry, Guru Nanak Dev University , Amritsar 143005, India.
J Org Chem ; 83(1): 57-68, 2018 01 05.
Article en En | MEDLINE | ID: mdl-29181970
Metal catalyzed post-Ugi cyclization of bis-amides is reported in this study. Exposure of bis-amides to Pd(II) catalyst triggered the formation of seven-membered benzoxazepinones. This investigation established that changing the catalyst to a Echavarren's gold(I) turned off cyclization to seven member ring and turned on 6-exo-dig annulations to afford family of six-membered benzoxazinones. To support the proposed mechanisms, quantum chemical based density functional theory calculations have been performed and validated. This novel method obtained molecular complexity up to four modular inputs and divergence of two different skeletons. 2D NMR spectroscopic techniques and single crystal X-ray diffraction established the proposed structures.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos
Texto completo
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Imprimir
XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: J Org Chem Año: 2018 Tipo del documento: Article País de afiliación: India Pais de publicación: Estados Unidos