通过溴代吡啶并[3,2-d]嘧啶-3(2H)-酮上的溴-镁交换反应合成功能化的哒嗪-3(2H)-酮。

Synthesis of functionalized pyridazin-3(2H)-ones via bromine-magnesium exchange on bromopyridazin-3(2H)-ones.

机构信息

Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, B-2020 Antwerp, Belgium.

出版信息

J Org Chem. 2009 Dec 18;74(24):9440-5. doi: 10.1021/jo9020985.

DOI:10.1021/jo9020985

Abstract

The potential of halogen-magnesium exchange reactions, followed by quenching with electrophiles, for the functionalization of the pyridazin-3(2H)-one core was investigated. 2-Benzyl-4-bromo-5-methoxy- (1), 2-benzyl-5-bromo-4-methoxy- (4), and 2-benzyl-4,5-dibromopyridazin-3(2H)-one (10) were selected as readily available model substrates. While 1 and 10 gave exclusively C-4 metalation, a tandem reaction involving nucleophilic substitution via addition elimination and bromine-magnesium exchange was observed with 4.

摘要

研究了卤镁交换反应，随后用亲电试剂进行淬灭，以实现哒嗪-3(2H)-酮核心的功能化。选择 2-苄基-4-溴-5-甲氧基-（1）、2-苄基-5-溴-4-甲氧基-（4）和 2-苄基-4,5-二溴哒嗪-3(2H)-酮（10）作为易得的模型底物。虽然 1 和 10 仅发生 C-4 金属化，但观察到 4 发生了涉及加成消除和溴镁交换的亲核取代的串联反应。

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