A Copper-Catalyzed N-Alkynylation Route to 2-Substituted N-Alkynyl Pyrroles and Their Cyclization into Pyrrolo[2,1-c]oxazin-1-ones: A Formal Total Synthesis of Peramine

被引：9

作者：

Reinus, Brandon J. ^{[1
]}

Kerwin, Sean M. ^{[2
]}

机构：

[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 USA

[2] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 11期

关键词：

cross-coupling; alkynes; nitrogen heterocycles; cyclization; peramine; COUPLING REACTIONS; ETHYL CYCLOPROPYLIDENEACETATE; ORGANIC-SYNTHESIS; ROOM-TEMPERATURE; TERMINAL ALKYNES; YNAMIDES; AMIDATION; BROMIDES; CYCLOADDITION; ARYL;

D O I：

10.1055/s-0036-1588736

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Screening of a variety of ligands and reaction conditions for the copper-catalyzed cross-coupling of alkynyl bromides with pyrroles, reveals that the use of the phenanthroline ligand 4,7-dimethoxy-1,10-phenanthroline affords a range of ynpyrroles in good to moderate yields. Furthermore, the utility of these ynpyrroles is demonstrated in the preparation of a series of pyrrolo[2,1-c][1,4]oxazin-1-ones and a formal total synthesis of the pyrrole natural product peramine.

引用

页码：2544 / 2554

页数：11

共 23 条

[21] Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N- versus C-Attack Paths
Kardile, Rahul Dadabhau
Liu, Rai-Shung
ORGANIC LETTERS, 2020, 22 (21) : 8229 - 8233
[22] Copper-Catalyzed Divergent C-H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines
Yang, Guang
Xiong, Zhicheng
Nie, Hongsheng
He, Meiqin
Feng, Qiong
Li, Xuan
Huang, Huabin
Wang, Shoucai
Ji, Fanghua
Jiang, Guangbin
ORGANIC LETTERS, 2022, 24 (09) : 1859 - 1864
[23] Efficient and Direct Route to 5-Iodo-4 H -Quinoxalines via Copper-Catalyzed Double C-N Arylations of 1,2,3-Triiodoarenes: Potential Application towards 5-Substituted 4 H -Quinoxalines
Al-Zoubi, Raed M.
Al-Jammal, Walid K.
Shkoor, Mohanad
Bani-Yaseen, Abdulilah D.
Ferguson, Michael J.
SYNTHESIS-STUTTGART, 2024, 56 (23): : 3680 - 3686

← 1 2 3 →