在溶液、无溶剂或固相条件下，通过1,2-二氮杂-1,3-丁二烯与1,2-二胺的反应直接合成吡嗪、哌嗪酮和喹喔啉。

Straightforward access to pyrazines, piperazinones, and quinoxalines by reactions of 1,2-diaza-1,3-butadienes with 1,2-diamines under solution, solvent-free, or solid-phase conditions.

作者信息

Aparicio Domitila, Attanasi Orazio A, Filippone Paolino, Ignacio Roberto, Lillini Samuele, Mantellini Fabio, Palacios Francisco, de Los Santos Jesús M

机构信息

Istituto di Chimica Organica, Università degli Studi di Urbino "Carlo Bo", Via Sasso 75, 61029 Urbino, Italy.

出版信息

J Org Chem. 2006 Aug 4;71(16):5897-905. doi: 10.1021/jo060450v.

DOI:10.1021/jo060450v

PMID:16872170

Abstract

The preparation of tetrahydropyrazines, dihydropyrazines, pyrazines, piperazinones, and quinoxalines by 1,4-addition of 1,2-diamines to 1,2-diaza-1,3-butadienes bearing carboxylate, carboxamide, or phosphorylated groups at the terminal carbon and subsequent internal heterocyclization is described. The solvent-free reaction of carboxylated 1,2-diaza-1,3-butadienes with the same reagents affords piperazinones, while phosphorylated 1,2-diaza-1,3-butadienes yield phosphorylated pyrazines. The solid-phase reaction of polymer-bound 1,2-diaza-1,3-butadienes with 1,2-diamines produces pyrazines.

摘要

描述了通过将1,2 - 二胺1,4 - 加成到在末端碳上带有羧酸盐、羧酰胺或磷酸化基团的1,2 - 二氮杂 - 1,3 - 丁二烯上，随后进行分子内杂环化来制备四氢吡嗪、二氢吡嗪、吡嗪、哌嗪酮和喹喔啉的方法。羧化的1,2 - 二氮杂 - 1,3 - 丁二烯与相同试剂的无溶剂反应得到哌嗪酮，而磷酸化的1,2 - 二氮杂 - 1,3 - 丁二烯则生成磷酸化的吡嗪。聚合物负载的1,2 - 二氮杂 - 1,3 - 丁二烯与1,2 - 二胺的固相反应产生吡嗪。