Citation: Yadavalli Suneel Kumar, Fazlur-Rahman Nawaz Khan. Chemo-selective Suzuki-Miyaura reactions: Synthesis of highly substituted [1, 6]-naphthyridines[J]. Chinese Chemical Letters, ;2017, 28(7): 1607-1612. doi: 10.1016/j.cclet.2017.02.007 shu

Chemo-selective Suzuki-Miyaura reactions: Synthesis of highly substituted [1, 6]-naphthyridines

Organic and Medicinal Chemistry Research Laboratory, School of Advanced Sciences, VIT-University, Vellore 632 014, India

Corresponding author: Fazlur-Rahman Nawaz Khan, nawazvit@gmail.com; nawaz_f@yahoo.co.in
Received Date: 20 November 2016
Revised Date: 19 January 2017
Accepted Date: 13 February 2017
Available Online: 16 July 2017

Figures(4)

The Suzuki-Miyaura reaction of methyl-5-bromo-8-(tosyloxy)-1, 6-naphthyridine-7-carboxylate (5), with 2 equiv. of arylboronic acids gave diarylated product, 5, 8-diaryl-1, 6-naphthyridine-7-carboxylate (7), whereas 1 equiv. of arylboronic acid resulted in site-selective formation of 5-aryl-8-(tosyloxy)-1, 6-naphthyridine-7-carboxylate (8). The reactions proceeded with excellent chemo-selectivity in favor of the bromide group. Likewise, one-pot reaction with completely different boronic acids by sequential addition produced 1, 6-naphthyridine-7-carboxylates, (10) containing two different aryl groups at 5 and 8 positions.
- Chemo-selective,
- Suzuki-Miyaura,
- [1, 6]-Naphthyridines,
- Site selective reaction,
- Diarylation Monoarylation
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