[Ag(PcL)]-Catalyzed Domino Reactions of 2-Alkynylbenzaldehydes with Electron-Poor Anilines: Synthesis of 1-Aminoisochromenes

被引：10

作者：

Pirovano, Valentina ^{[1
]}

Hamdan, Gabriele ^{[1
]}

Garanzini, Davide ^{[1
]}

Brambilla, Elisa ^{[1
]}

Rossi, Elisabetta ^{[1
]}

Caselli, Alessandro ^{[2
,3
]}

Abbiati, Giorgio ^{[1
]}

机构：

[1] Univ Milan, Sez Chim Gen & Organ A Marchesini, Dipartimento Sci Farmaceut, Via Venezian 21, I-20133 Milan, Italy

[2] Univ Milan, Dipartimento Chim, Via Golgi 19, I-20133 Milan, Italy

[3] CNR, SCITEC, Via Golgi 19, I-20133 Milan, Italy

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 17期

关键词：

Isochromenes; Alkynes; Domino reactions; Silver; Electron-poor anilines; Macrocyclic ligands; CYCLIC ALKENYL ETHERS; O-ALKYNYLBENZALDEHYDES; LEWIS-ACID; CYCLIZATION; HETEROCYCLES; ALKYNES; SILVER; ISOQUINOLINES; DERIVATIVES; CATALYST;

D O I：

10.1002/ejoc.202000275

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we describe the synthesis of neglected 1-aminoisochromene derivatives starting from 2-alkynylbenzaldehydes and electron-poor anilines. The domino reaction is catalyzed by original [(AgPcL)-Pc-I] complexes and occurs with complete regioselectivity under mild conditions. The approach well-tolerates different aryl, heteroaryl, alkyl and cycloalkyl substituents on alkyne terminus to give the desired products in modest to very good yields.

引用

页码：2592 / 2599

页数：8

共 46 条

[1] PdCl2-Catalyzed Domino Reactions of 2-Alkynylbenzaldehydes with Indoles: Synthesis of Fluorescent 5H-Benzo[b]carbazol-6-yl Ketones
Tang, Ri-Yuan
Li, Jin-Heng
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (16) : 4733 - 4738
[2] Synthesis of Isoquinoline-Fused Quinazolinones through Ag(I)-Catalyzed Cascade Annulation of 2-Aminobenzamides and 2-Alkynylbenzaldehydes
Sonawane, Amol D.
Shaikh, Yunnus B.
Garud, Dinesh R.
Koketsu, Mamoru
SYNTHESIS-STUTTGART, 2019, 51 (02): : 500 - 507
[3] NHC-Catalyzed Oxidative Cyclization Reactions of 2-Alkynylbenzaldehydes under Aerobic Conditions: Synthesis of O-Heterocycles
Park, Jong Hyub
Bhilare, Sachin V.
Youn, So Won
ORGANIC LETTERS, 2011, 13 (09) : 2228 - 2231
[4] PHOTOCYCLOADDITION REACTIONS OF 1,4-BENZOXAZIN-2-ONES AND ELECTRON-POOR OLEFINS
NISHIO, T
OMOTE, Y
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09): : 1370 - 1373
[5] Synthesis of 1-(1H-Indol-3-yl)-1,2-dihydroisoquinolines via AgOTf-Catalyzed Three-Component Reactions of 2-Alkynylbenzaldehydes, Amines, and Indoles
Yu, Xingxin
Wu, Jie
JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (02): : 238 - 244
[6] SYNTHESIS AND REACTIVITY OF ELECTRON-POOR 2-AZADIENES - [4+2] CYCLOADDITION REACTIONS WITH ALKENES AND ENAMINES
PALACIOS, F
DEHEREDIA, IP
RUBIALES, G
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08): : 2384 - 2390
[7] Palladium(II) Chloride-Catalyzed Aerobic Oxidative Intermolecular Cycloaddition Reaction of 2-Alkynylbenzaldehydes and Electron-Deficient Terminal Alkenes: An Efficient Synthesis of Naphthyl Ketones
Janreddy, Donala
Kavala, Veerababurao
Kotipalli, Trimurtulu
Kuo, Chun-Wei
Kuo, Ting-Shen
Chen, Mei-Ling
He, Chiu-Hui
Yao, Ching-Fa
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) : 3083 - 3091
[8] Ag(I)-Catalyzed Synthesis of 2-Aminoquinolines from 1-Aminobutadiynes and Anilines
Liu, Ningning
Sun, Huaming
Wang, Junying
Zhang, Zunting
Wang, Tao
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (24) : 5443 - 5447
[9] AgOTf-catalyzed three-component reactions of 2-alkynylbenzaldehydes, amines, and diethylphosphite. An efficient route to 2,3-disubstituted-1,2-dihydroisoquinolin-1-ylphosphonates
Sun, Wei
Ding, Qiuping
Sun, Xiaoyu
Fan, Renhua
Wu, Jie
JOURNAL OF COMBINATORIAL CHEMISTRY, 2007, 9 (04): : 690 - 694
[10] Total Synthesis of Methyl 1,5,8-Trimethoxy-1H-isochromene-3-carboxylate and Its Derivatives via Palladium-Catalyzed Annulation of 2-Alkynylbenzaldehydes
Nardangeli, Nolan
Thomson, Jared
Topolovcan, Nikola
Hudlicky, Tomas
SYNTHESIS-STUTTGART, 2021, 53 (21): : 4110 - 4116

← 1 2 3 4 5 →