Regioselective Nucleophilic Substitution of 5‐Bromo‐2‐methoxytropone. Issue 6 (28th June 2014)

• Record Type: Journal Article
• Authors: Sato, Ohki; Nitta, Ai; Yamamoto, Ami
• Is Part Of: Heteroatom chemistry. Volume 25:Issue 6(2014:Nov.)
• Page Start: 644
• Page End: 650
• Publication Date: 2014-06-28
• Subjects: Heterocyclic chemistry -- Periodicals; 547.59
• DOI: 10.1002/hc.21201
• Languages: English
• ISSNs: 1042-7163

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>The reaction of 5‐bromo‐2‐methoxytropone with <italic>O</italic>‐ and <italic>N</italic>‐nucleophiles, such as ethanol/potassium carbonate, sodium hydroxide, diethylamine, propylamine, <italic>p</italic>‐chloroaniline/triethylamine, and <italic>p</italic>‐phenylenediamine/triethylamine, gave corresponding 2‐<italic>O</italic>‐ and 2‐<italic>N</italic>‐substituted troponoids. Alkyl diamines reacted with the substrate to produce bis(2‐aminotropone)s. In the case of <italic>S</italic>‐nucleophiles as 1‐propanethiol, thiophenol, and 4‐aminothiophenol with a base, the regioselective substitution at the 5‐position occurred. Halogenation reagents, triphenyldibromophosphorane and its dichloro analogue, furnished 2, 5‐dibromo‐ and 2, 5‐dichlorotropones, respectively.</p> </abstract>