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A Formal [5+1] Annulation Reaction of Sulfur Ylides and 2‐(1 H ‐indol‐2‐yl)phenols: Access to Indole‐Fused 4 H ‐benzo[ e ][1,3]oxazines
Author(s) -
Jia Penghao,
Huang You
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800573
Subject(s) - chemistry , synthon , annulation , thioether , indole test , phenols , moiety , sulfur , salt (chemistry) , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The first sulfur ylides involved formal [5+1]‐annulation reaction was developed between prop‐2‐ynylsulfonium salts and 2‐(1 H ‐indol‐2‐yl)phenols. Prop‐2‐ynylsulfonium salt participates in the reaction with its β‐carbon atom and acts as a novel C 1 synthon. Various indole‐fused 4 H ‐benzo[ e ][1,3]oxazines bearing a thioether moiety were constructed in good to high yields under mild conditions.