An Efficient Synthesis of Quinazolines: a Theoretical and Experimental Study on the Photochemistry of Oxime Derivatives

  1. Alonso, R. 1
  2. Caballero, A. 1
  3. Campos, P.J. 1
  4. Sampedro, D. 1
  5. Rodríguez, M.A. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron

ISSN: 0040-4020

Any de publicació: 2010

Volum: 66

Número: 25

Pàgines: 4469-4473

Tipus: Article

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DOI: 10.1016/J.TET.2010.04.082 SCOPUS: 2-s2.0-77953122297 WoS: WOS:000278947100008 GOOGLE SCHOLAR

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Resum

A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2). © 2010 Elsevier Ltd. All rights reserved.