AN EFFICIENT METHOD FOR THE SYNTHESIS OF N-ARYL SUBSTITUTED C1-FUNCTIONALIZED 1,2,3,4-TETRAHYDROISOQUINOLINES

被引：0

作者：

Luo, Hairong ^{[1
]}

Tian, Fen ^{[2
]}

He, Yi ^{[1
]}

Liu, Xurong ^{[1
]}

Li, Jing ^{[1
]}

Chen, Meihang ^{[1
]}

机构：

[1] Tongren Univ, Coll Mat & Chem Engn, Tongren 554300, Peoples R China

[2] Tongren Univ, Sch Sports & Hlth Sci, Tongren 554300, Peoples R China

来源：

HETEROCYCLES | 2022年 / 104卷 / 09期

关键词：

ASYMMETRIC-SYNTHESIS; COUPLING REACTION; MANNICH REACTION; 3-COMPONENT; DERIVATIVES; ALKALOIDS; AMINES; BONDS;

D O I：

10.3987/COM-22-14697

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and facile cyclic iminium-ion-based strategy has been developed for the synthesis of structurally diverse N-aryl substituted C1-functionalized THIQs. Cyclic iminium ions generated in situ from 2-(2-bromomethyl)benzaldehyde reacted with acetone to furnish ketone moiety at C-1 position in THIQs in moderate to good yields.

引用

页码：1641 / 1648

页数：8

共 38 条

[1]

Barbosa-Filho José M., 2006, Rev. bras. farmacogn., V16, P109, DOI 10.1590/S0102-695X2006000100020

[2] Highly Stereoselective and Scalable Synthesis of trans-Fused Octahydrocyclohepta[b]pyrrol-4(1H)-ones via the Aza-Cope-Mannich Rearrangement in Racemic and Enantiopure Forms [J].

Belov, Dmitry S. ;

Lukyanenko, Evgeny R. ;

Kurkin, Alexander V. ;

Yurovskaya, Marina A. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (22) :10125-10134

[3] Mechanistic Studies on a Cu-Catalyzed Aerobic Oxidative Coupling Reaction with N-Phenyl Tetrahydroisoquinoline: Structure of Intermediates and the Role of Methanol As a Solvent [J].

Boess, Esther ;

Sureshkumar, Devarajulu ;

Sud, Abhishek ;

Wirtz, Cornelia ;

Fares, Christophe ;

Klussmann, Martin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (21) :8106-8109

[4] Biomedical Application of Orexin/Hypocretin Receptor Ligands in Neuroscience [J].

Boss, Christoph ;

Brisbare-Roch, Catherine ;

Jenck, Francois .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (04) :891-903

[5] Proline catalyzed, one-pot three component Mannich reaction and sequential cyclization toward the synthesis of 2-substituted piperidine and pyrrolidine alkaloids [J].

Chacko, Shibin ;

Ramapanicker, Ramesh .

TETRAHEDRON LETTERS, 2015, 56 (15) :2023-2026

[6] Novel indolizino[8,7-b]indole hybrids as anti-small cell lung cancer agents: Regioselective modulation of topoisomerase II inhibitory and DNA crosslinking activities [J].

Chang, Sue-Ming ;

Christian, Wilson ;

Wu, Ming-Hsi ;

Chen, Tai-Lin ;

Lin, Yi-Wen ;

Suen, Ching-Shu ;

Pidugu, Hima Bindu ;

Detroja, Dilip ;

Shah, Anamik ;

Hwang, Ming-Jing ;

Su, Tsann-Long ;

Lee, Te-Chang .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 127 :235-249

[7] Asymmetric synthesis of isoquinoline alkaloids [J].

Chrzanowska, M ;

Rozwadowska, MD .

CHEMICAL REVIEWS, 2004, 104 (07) :3341-3370

[8] Organocatalysis with proline derivatives: improved catalysts for the asymmetric Mannich, nitro-Michael and aldol reactions [J].

Cobb, AJA ;

Shaw, DM ;

Longbottom, DA ;

Gold, JB ;

Ley, SV .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (01) :84-96

[9] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].

Córdova, A ;

Notz, W ;

Zhong, GF ;

Betancort, JM ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843

[10] CARDIOVASCULAR EFFECTS OF SUBSTITUTED TETRAHYDROISOQUINOLINES IN RATS [J].

DONG, H ;

LEE, CM ;

HUANG, WL ;

PENG, SX .

BRITISH JOURNAL OF PHARMACOLOGY, 1992, 107 (01) :262-268

← 1 2 3 4 →