121726-08-7Relevant articles and documents
Synthese de dialdehydes-1,5 dieniques par reaction en milieu acide, d'aldehydes aromatiques avec le methoxy-2 dihydro-3,4 2H-pyranne
Lepage, Lucette,Lepage, Yves
, p. 591 - 594 (2007/10/02)
A convenient synthesis for 1,5-dicarboxaldehydes by condensation of pentanedial 4 (produced in situ by 2-methoxy-3,4-dihydro-2H-pyran 3 hydrolysis in aqueous acetic acid) with benzaldehydes and aromatic orthodialdehydes is reported.Electron withdrawing subtituents on benzaldehydes seem necessary to achieve the condensation ; (E,E)-2,4-bisphenyl-methylenepentanedials 6a-g are obtained.Phthalaldehydes 1a-b, naphthalaldehydes 10a-b, furandicarboxaldehydes 12a-c give respectively dicarboxaldehydes 8a-b, 11a-b and 13a-c.The annulene 9 is obtained from the reaction between 7H-benzo(c)cycloheptene-6,8-dicarboxaldehyde (8a) and an excess of pyran 3.The new dicarboxaldehydes 10b and 14 are prepared by condensation of 4,5-dibenzoylphthalaldehyde 1b and 1,4-dioxobutane (from 2,5-dimethoxy-tetrahydrofuran 7).The reaction between 1,5-dialdehydes 8a and 11a and an excess of hydrazine gives the bishydrazones.