[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

[21] SYNTHESIS OF 4-OXO-4H-BENZOTHIAZOLO[3,2-A]PYRIMIDIN-1-IUM-2-OLATES AND THEIR CYCLO-ADDITION REACTIONS TO ELECTRON-POOR AND ELECTRON-RICH ALKYNES AS WELL AS TO ORTHO-CHLORANIL
GOTTHARDT, H
BLUM, J
CHEMISCHE BERICHTE-RECUEIL, 1985, 118 (05): : 2079 - 2094
[22] Domino reaction of anilines with 3,4-dihydro-2H-pyran catalyzed by cation-exchange resin in water: an efficient synthesis of 1,2,3,4-tetrahydroquinoline derivatives
Chen, L
Li, CJ
GREEN CHEMISTRY, 2003, 5 (05) : 627 - 629
[23] Synthesis of Functionalized 3-(1H-Isochromen)-chromones via Ag2O-Catalyzed Cascade Cyclization Reaction of o-Hydroxyarylenaminones with o-Alkynylbenzaldehydes
Zhang, Mingshuai
Liu, Zhuoyuan
Chen, Longkun
Liu, Donghan
Sun, Yulin
Chai, Zhangmengjie
Chen, Xue-Bing
Yu, Fuchao
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (24) : 4440 - 4446
[24] Synthesis of 2,5-bis-arylpyridines by [4+2] cycloaddition of 1,4-bis aryl-2-aza-1,3-butadienes with electron-poor dienophiles
Paparin, JL
Crévisy, C
Grée, R
Toupet, L
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (02) : 411 - 418
[25] Electron-Poor, Fluoro-Containing Arylboronic Acids as Efficient Coupling Partners for Bis(1,5-cyclooctadiene)nickel(0)/Tricyclohexylphosphine-Catalyzed Cross-Coupling Reactions of Aryl Arenesulfonates
Chen, Wen-Bo
Xing, Chun-Hui
Dong, Jie
Hu, Qiao-Sheng
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (13) : 2072 - 2076
[26] Pd(OAc)2-catalyzed domino reactions of 1,2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents:: efficient synthesis of substituted fluorenes
Dong, Cheng-Guo
Hu, Qiao-Sheng
TETRAHEDRON, 2008, 64 (11) : 2537 - 2552
[27] SYNTHESIS OF 2,6-DIAZABICYCLO[2.2.2]OCTANE-3,5-DIONE DERIVATIVES AND 2(1H)-PYRIDINONES - A CONTRIBUTION TO THE REGIOCHEMISTRY AND STEREOSPECIFICITY OF 1,4-DIPOLAR CYCLOADDITION REACTIONS OF PYRIMIDINIUM-4-OLATES TO ELECTRON-RICH AND ELECTRON-POOR ALKENES
GOTTHARDT, H
BLUM, J
CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (01): : 109 - 114
[28] Transition-Metal-Catalyzed Domino Reactions: Efficient One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans from Electron-Deficient Alkynes and 2-Yn-1-ols
Cao, Hua
Jiang, Huanfeng
Huang, Huawen
SYNTHESIS-STUTTGART, 2011, (07): : 1019 - 1036
[29] Synthesis of [6,7]-dihydro-[1,4]-dioxino-[2,3-f][2,1,3]-benzothiadiazole: A Novel building block for electron-poor conjugated polymers
Sun Xiaoxia
Zhuang Xiaoxiao
Li Yingchun
Liu Ximei
Lou Yazhou
MATERIALS AND DESIGN, PTS 1-3, 2011, 284-286 : 601 - 606
[30] ALPHA-METHYL FUNCTIONALIZATION OF ELECTRON-POOR HETEROCYCLES - 2,9-BIS(CHLOROMETHYL)-1,10-PHENANTHROLINE - SYNTHESIS OF A [3.3)CYCLOPHANE CONTAINING THE 1,10-PHENANTHROLINO MOIETY
NEWKOME, GR
KIEFER, GE
PUCKETT, WE
VREELAND, T
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25): : 5112 - 5114

← 1 2 3 4 5 →