Concise Synthesis of [1,1′-Biisoquinoline]-4,4′-diol via a Protecting Group Strategy and Its Application for Potential Liquid-Crystalline Compounds
✍ Scribed by Elisabeth Kapatsina; Markus Mateescu; Angelika Baro; Wolfgang Frey; Sabine Laschat
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- German
- Weight
- 263 KB
- Volume
- 92
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The [1,1′‐biisoquinoline]‐4,4′‐diol (4a), which was obtained as hydrochloride 4a⋅2 HCl in two steps starting from the methoxymethyl (MOM)‐protected 1‐chloroisoquinoline 8 (Scheme 3), opens access to further O‐functionalized biisoquinoline derivatives. Compound 4a⋅2 HCl was esterified with 4‐(hexadecyloxy)benzoyl chloride (5b) to give the corresponding diester 3b (Scheme 4), which could not be obtained by Ni‐mediated homocoupling of 6b (Scheme 2). The ether derivative 2b was accessible in good yield by reaction of 4a⋅2 HCl with the respective alkyl bromide 9 under the conditions of Williamson etherification (Scheme 4). Slightly modified conditions were applied to the esterification of 4a⋅2 HCl with galloyl chlorides 10a–h as well as etherification of 4a⋅2 HCl with 6‐bromohexyl tris(alkyloxy)benzoates 11b,d–h and [(6‐bromohexyl)oxy]‐substituted pentakis(alkyloxy)triphenylenes 14a–c (Scheme 5). Despite the bulky substituents, the respective target 1,1′‐biisoquinolines 12, 13, and 15 were isolated in 14–86% yield (Table).