Synthesis 2022; 54(08): 2070-2080
DOI: 10.1055/a-1707-2924
paper

Phosphonium-Mediated Synthesis of a New Class of Indoloquinazoline Derivatives Bearing a C-12 Aryloxy Ester or Spiro-γ-lactone

Nittaya Wiriya
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
,
Mookda Pattarawarapan
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
b   Environmental, Occupational Health Sciences and Non-Communicable Diseases Center of Excellence, Chiang Mai University, Chiang Mai, 50200, Thailand
,
Saranphong Yimklan
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
,
Surat Hongsibsong
b   Environmental, Occupational Health Sciences and Non-Communicable Diseases Center of Excellence, Chiang Mai University, Chiang Mai, 50200, Thailand
c   School of Health Science Research, Research Institute for Health Science, Chiang Mai University, Chiang Mai, 50200, Thailand
,
a   Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand
b   Environmental, Occupational Health Sciences and Non-Communicable Diseases Center of Excellence, Chiang Mai University, Chiang Mai, 50200, Thailand
› Institutsangaben
This work was partially supported by Chiang Mai University, Thailand and the Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program (Grant No. PHD/0072/2559) to N.W.


Abstract

Indoloquinazolines functionalized at C-12, which are structural analogs of the natural alkaloid cephalanthrin B, are readily constructed via Ph3P/I2-mediated one-pot reactions of isatins with aromatic alcohols. In the presence of excess phenols, the C-12 aryloxy ester products are obtained in moderate to good yields under mild conditions. Moreover, fused bicyclic hydroxyaryl derivatives such as 8-hydroxyquinoline give rise to novel C-12 spiro-γ-lactone derivatives. A reactive iminium cation species derived from dehydration of the C-12 hydroxy ester precursor is proposed as the transient intermediate responsible for these transformations.

Supporting Information



Publikationsverlauf

Eingereicht: 01. November 2021

Angenommen nach Revision: 26. November 2021

Publikationsdatum:
26. November 2021 (online)

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