Intermolecular Nucleophilic Addition of N-Diaminophosphinoyl-Protected α-Carbanions Derived from Secondary Amines to Arynes: Synthesis of 1-Aryl-1,2,3,4-tetrahydroisoquinolines

被引：6

作者：

Singh, Kamal N. ^{[1
,2
]}

Singh, Paramjit ^{[1
,2
]}

Kaur, Manjot ^{[1
,2
]}

Sharma, Esha ^{[1
,2
]}

机构：

[1] Panjab Univ, Dept Chem, Chandigarh 160014, India

[2] Panjab Univ, Ctr Adv Studies Chem, Chandigarh 160014, India

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 07期

关键词：

alpha-Amino carbanion; Arylation; 1-Aryl-1,2,3,4tetrahydroisoquinolines; Benzyne; Intermolecular nucleophilic addition; Secondary amines; PICTET-SPENGLER REACTIONS; ONE-POT SYNTHESIS; H BOND ARYLATION; IN-SITU IR; C-H; 1-SUBSTITUTED TETRAHYDROISOQUINOLINES; ASYMMETRIC-SYNTHESIS; BORONIC ACIDS; DERIVATIVES; ALKYLATION;

D O I：

10.1002/slct.201700051

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Various 1-aryl-1,2,3,4-tetrahydroisoquinolineswere synthesized by coupling a-amino carbanions, derived from N-protected secondary amines, with in situ generated arynes. Different N-protecting/ activating groups were investigated and it was found that only the N-bis(dimethylamino) phosphinoyl group is suitable to obtain the title compounds. This procedure has also been used for an efficient one-pot synthesis of the drug (+/-)FR115427.

引用

页码：2213 / 2218

页数：6

共 91 条

[1] Synthesis and neurotoxicity of tetrahydroisoquinoline derivatives for studying Parkinson's disease [J].

Abe, K ;

Saitoh, T ;

Horiguchi, Y ;

Utsunomiya, I ;

Taguchi, K .

BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2005, 28 (08) :1355-1362

[2]

[Anonymous], MODERN ARYLATION MET

[3] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids [J].

Basle, Olivier ;

Li, Chao-Jun .

ORGANIC LETTERS, 2008, 10 (17) :3661-3663

[4] METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].

BEAK, P ;

ZAJDEL, WJ ;

REITZ, DB .

CHEMICAL REVIEWS, 1984, 84 (05) :471-523

[5] Tetrahydroisoquinolines as dopaminergic ligands: 1-Butyl-7-chloro-6-hydroxy-tetrahydroisoquinoline, a new compound with antidepressant-like activity in mice [J].

Berenguer, Inmaculada ;

El Aouad, Noureddine ;

Andujar, Sebastian ;

Romero, Vanessa ;

Suvire, Fernando ;

Freret, Thomas ;

Bermejo, Almudena ;

Dolores Ivorra, Maria ;

Enriz, Ricardo D. ;

Boulouard, Michel ;

Cabedo, Nuria ;

Cortes, Diego .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (14) :4968-4980

[6] Enantioselective, palladium-catalyzed α-arylation of N-Boc-pyrrolidine [J].

Campos, KR ;

Klapars, A ;

Waldman, JH ;

Dormer, PG ;

Chen, CY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (11) :3538-3539

[7] A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate [J].

Chen, Wenfang ;

Zheng, Hongbo ;

Pan, Xinhui ;

Xie, Zhiyu ;

Zan, Xin ;

Sun, Bin ;

Liu, Lei ;

Lou, Hongxiang .

TETRAHEDRON LETTERS, 2014, 55 (17) :2879-2882

[8] 1-aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro [J].

Cheng, Pi ;

Huang, Ning ;

Jiang, Zhi-Yong ;

Zhang, Quan ;

Zheng, Yong-Tang ;

Chen, Ji-Jun ;

Zhang, Xue-Mei ;

Ma, Yun-Bao .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (07) :2475-2478

[9] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].

COX, ED ;

COOK, JM .

CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842

[10] Abnormal products in the Bischler-Napieralski isoquinoline synthesis [J].

Doi, S ;

Shirai, N ;

Sato, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (15) :2217-2221

← 1 2 3 4 5 6 7 8 9 10 →