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Synthesis 2022; 54(08): 2070-2080
DOI: 10.1055/a-1707-2924
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
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
- Supporting information for this article is available online at https://doi.org/10.1055/a-1707-2924.
- Supporting Information
Publication History
Received: 01 November 2021
Accepted after revision: 26 November 2021
Accepted Manuscript online:
26 November 2021
Article published online:
25 January 2022
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