Metal-Free -C(sp3)-H Functionalized Oxidative Cyclization of Tertiary N,N-Diarylamino Alcohols: Construction of N,N-Diarylaminotetrahydropyran Scaffolds

被引：11

作者：

Afzal, Sualiha ^{[1
,2
]}

Venkanna, Arramshetti ^{[1
,2
]}

Park, Hyeung-geun ^{[3
,4
]}

Kim, Mi-hyun ^{[1
,2
]}

机构：

[1] Gachon Univ, Coll Pharm, Gachon Inst Pharmaceut Sci, 155 Gaetbeol Ro, Inchon, South Korea

[2] Gachon Univ, Coll Pharm, Dept Pharm, 155 Gaetbeol Ro, Inchon, South Korea

[3] Seoul Natl Univ, Pharmaceut Sci Res Inst, Seoul 151, South Korea

[4] Seoul Natl Univ, Coll Pharm, Seoul 151, South Korea

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 02期

关键词：

6-exo-trig; metal-free reactions; oxidative cyclization; tertiary amines; -C(sp(3))-H functionalization; C-H ACTIVATION; DIRECTING-GROUP; NITROGEN ATOM; AMINES; IODINE; BONDS; DERIVATIVES; MECHANISM; SCOPE; QUINOLINES;

D O I：

10.1002/ajoc.201500392

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an efficient synthetic method for the preparation of anomeric N,N-diarylaminotetrahydropyran scaffolds. The free radical 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)/hypervalent iodine(III)- or TEMPO/I-2-mediated oxidative cyclization of tertiary amino alcohols was used to construct N,N-diarylaminotetrahydropyrans through -C(sp(3))-O bond formation, with the loss of only two Hatoms. This efficient synthetic method broadens the scope of viable -C(sp(3))-H functionalized amines to include conformational-bias-free substrates.

引用

页码：232 / 239

页数：8

共 44 条

[1]

[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANIE.201201666

[2] Oxidative synthesis of cyclic acyl aminals through carbon-carbon σ-bond activation [J].