Synthesis
DOI: 10.1055/a-1707-2924
paper

Phosphonium-mediated synthesis of a new class of indoloquinazoline derivatives bearing C-12 aryloxy ester and spiro-γ-lactone

Nittaya Wiriya
1  Chemistry, Chiang Mai University, Chiang Mai, Thailand
,
Mookda Pattarawarapan
2  Department of Chemistry, Chiang Mai University, Chiang Mai, Thailand
,
Saranphong Yimklan
1  Chemistry, Chiang Mai University, Chiang Mai, Thailand
,
Surat Hongsibsong
3  School of Health Science Research, Research Institute for Health Science, cSchool of Health Science Research, Research Institute for Health Science, Chiang Mai University, 50200, Thailand, Chiang Mai, Thailand
,
4  Chemistry, Chiang Mai University, Chiang Mai, Thailand
› Author Affiliations

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



Publication History

Received: 01 November 2021

Accepted after revision: 26 November 2021

Publication Date:
26 November 2021 (online)

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