skip to main content
Idioma:
Tipo de recurso Mostra resultados com: Mostra resultados com: Índice

Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Piperidinoquinones, Highly Substituted Dihydrophenanthridines, Benzophenanthridines, and the Naturally Occurring Pyrrolophenanthridine, Assoanine

Xiong, Yifeng ; Moore, Harold W

Journal of organic chemistry, 1996-12, Vol.61 (26), p.9168-9177 [Periódico revisado por pares]

American Chemical Society

Texto completo disponível

Citações Citado por
  • Título:
    Ring Expansion of 4-Alkynylcyclobutenones. Synthesis of Piperidinoquinones, Highly Substituted Dihydrophenanthridines, Benzophenanthridines, and the Naturally Occurring Pyrrolophenanthridine, Assoanine
  • Autor: Xiong, Yifeng ; Moore, Harold W
  • É parte de: Journal of organic chemistry, 1996-12, Vol.61 (26), p.9168-9177
  • Notas: Abstract published in Advance ACS Abstracts, December 15, 1996.
    ark:/67375/TPS-2D3F1T2D-F
    istex:C569982224FD83C2A8799116CF887D7CB9BB317A
  • Descrição: New synthetic routes to a variety of N-heterocyclic quinones and hydroquinones are described. These include thermolyses of 4-hydroxy-4-[4-N-(benzenesulfonyl)-4-aza-1,6-dialkynyl]cyclobutenones to piperidinoquinones and 4-hydroxy-4-[3-(N-phenylamino)-1-propynyl]cyclobutenones to dihydrophenanthridinediols. Included in the array of products available by this method are benzophenanthridines, indolophenanthridines, isoindoloindoles, and pyrrolophenanthridines. The methodology was employed in a five-step synthesis of the alkaloid assoanine starting with dimethyl squarate and indoline. The key step in all of these transformations is the ring expansion of appropriately substituted 4-hydroxy-4-alkynylcyclobutenones. These are envisaged to undergo electrocyclic ring opening to the corresponding enynylketenes which ring close to diradical intermediates that then lead to products via either radical additions to proximal alkyne moieties or undergo homolytic aromatic substitution to appropriately placed aryl groups. The synthetic scope and mechanism of the ring expansion reactions are discussed.
  • Editor: American Chemical Society
  • Idioma: Inglês
Voltar para lista de resultados

  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

Buscando em bases de dados remotas. Favor aguardar.