Pd-catalyzed Cyclization of Terminal Alkynes using Diazonaphthoquinones: Synthesis of Naphtho[1,2-b]furans

被引：5

作者：

Takahashi, Shuhei ^{[1
]}

Shimooka, Hirokazu ^{[1
]}

Okauchi, Tatsuo ^{[1
]}

Kitamura, Mitsuru ^{[1
]}

机构：

[1] Kyushu Inst Technol, Dept Appl Chem, Grad Sch Engn, 1-1 Sensuicho, Kitakyushu, Fukuoka 8048550, Japan

来源：

CHEMISTRY LETTERS | 2019年 / 48卷 / 01期

关键词：

Diazo compound; Palladium; Naphthofuran; C-H FUNCTIONALIZATION; REGIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; INSERTION REACTIONS; N-TOSYLHYDRAZONES; O-ALKYNYLPHENOLS; DIRECT ARYLATION; DIAZO-COMPOUNDS; BOND FORMATION; CONSTRUCTION;

D O I：

10.1246/cl.180803

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Naphtho[1,2-b]furans were synthesized via a Pd-catalyzed reaction of diazonaphthoquinones and terminal alkynes in the presence of CuI and diisopropylamine. This method was then successfully applied to the synthesis of natural product, furomollugin.

引用

页码：28 / 31

页数：4

共 50 条

[41] Synthesis of Naphtho[1′,2′:4,5]imidazo[1,2-α]pyridines and imidazo[5,1,2-cd]indolizines Through Pd-Catalyzed Cycloaromatization of 2-Phenylimidazo[1,2-α]pyridines with Alkynes
Li, Peiyuan
Zhang, Xinying
Fan, Xuesen
JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (15): : 7508 - 7518
[42] Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization
Yue, DW
Yao, TL
Larock, RC
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (25): : 10292 - 10296
[43] 1,2-Palladasilacyclobutene: The Missing Link in the Pd-Catalyzed Annulation of Alkynes for the Silirene-to-Silole Transformation
Devillard, Marc
Dinoi, Chiara
Del Rosal, Iker
Orione, Clement
Cordier, Marie
Alcaraz, Gilles
INORGANIC CHEMISTRY, 2023, 62 (19) : 7250 - 7263
[44] Pd-Catalyzed B-H Aryl/Alkenylation of 1,2-Azaborines
Zhang, Zhen
Jiang, Dandan
Su, Peiwen
Yang, Kai
Yu, Peiyuan
Song, Qiuling
ACS CATALYSIS, 2024, 14 (22): : 16996 - 17003
[45] Direct Access to α,β-Alkynylamides via Pd-Catalyzed Carbonylation of Terminal Alkynes with Amines Using Chloroform as the CO Surrogate
Rathod, Gajanan K. K.
Jain, Rahul
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 7219 - 7227
[46] Synthesis and In Vitro Anti-inflammatory Activity of Pyrrolo[1,2-a]pyrazines via Pd-catalyzed Intermolecular Cyclization Reaction
Zhou, Yanmei
Wei, Yong
Yang, Jin
Li, Haihai
Liu, Miaodeng
Huang, Nianyu
ADVANCED RESEARCH ON MATERIAL ENGINEERING, CHEMISTRY, BIOINFORMATICS III, 2014, 830 : 115 - 118
[47] Enantioselective formal synthesis of (-)-aurantioclavine using Pd-catalyzed cascade cyclization and organocatalytic asymmetric aziridination
Nakano, Shun-ichi
Hamada, Yasumasa
Nemoto, Tetsuhiro
TETRAHEDRON LETTERS, 2018, 59 (08) : 760 - 762
[48] Pd-Catalyzed Regioselective 1,2-Dicarbofunctionalization of Unactivated Olefins by a Heck Reaction/Enolate Cyclization Cascade
Dhungana, Roshan K.
Shrestha, Bijay
Thapa-Magar, Rajani
Basnet, Prakash
Giri, Ramesh
ORGANIC LETTERS, 2017, 19 (08) : 2154 - 2157
[49] A Single-Step Synthesis of Stereodefined Skipped Trienes: Pd-Catalyzed Cascade Reaction of Terminal Alkynes with Allylic Halides
Bai, Peizhi
Jiang, Yubo
Xiao, Tiebo
Qin, Guiping
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (18)
[50] RESEARCH ON NITRO-DERIVATIVES OF BIOLOGICAL INTEREST .44. SYNTHESIS OF 2-NITRO-NAPHTHO[1,2-B]FURANS MONOMETHOXYLATED ON THE EXTERNAL HOMOCYCLE
BILGER, C
DEMERSEMAN, P
ROYER, R
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1987, 22 (04) : 363 - 365

← 1 2 3 4 5 →