✦ LIBER ✦

Rearrangements during aminations of bromo-1,5-naphthyridines, probably involving a naphthyridyne as an intermediate

✍ Scribed by W. Czuba

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 529 KB
Volume: 82
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19630821008

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

When reacted with potassium amide in liquid ammonia both 3‐bromo‐and 4‐bromo‐1,5‐naphthyridine are converted into a mixture containing 3‐amino‐ and 4‐amino‐1,5‐naphthyridine. The course of these reactions can be explained by a mechanism involving 1,5‐naphthyridyne‐3,4 as an intermediate.

An abnormal reaction takes place during the aminations of 2‐bromo‐1,5‐naphthyridine, a compound, C~8~H~8~N~4~, together with the chief product 2‐amino‐1,5‐naphthyridine and 1,5‐naphthyridine being formed.

In the case of 3‐bromo‐2‐ethoxy‐1,5‐naphthyridine an amination reaction afforded only 3‐amino‐2‐ethoxy‐1,5‐naphthyridine. Syntheses of 3‐bromo‐2‐ethoxy‐1,5‐naphthyridine and 3‐amino‐2‐ethoxy‐1,5‐naphthyridine are described.

📜 SIMILAR VOLUMES

Aminations of bromo-derivatives of 4-eth

Aminations of bromo-derivatives of 4-ethoxy- and 2,4-diethoxy-pyridine, probably involving a 2,3-pyridyne as intermediate

✍ M. J. Pieterse; H. J. den Hertog 📂 Article 📅 2010 🏛 Elsevier Science 🌐 English ⚖ 443 KB

## Abstract The amination of 3‐bromo‐4‐ethoxypyridine with potassium amide in liquid ammonia yielding 2‐amino‐4‐ethoxypyridine as chief product has been reinvestigated. It is shown that 2‐amino‐5‐bromo‐4‐ethoxypyridine is formed as a byproduct, probably __via__ 3,5‐dibromo‐4‐ethoxypyridine and 5‐br