TBAB-mediated radical 6-endo-trig ortho-cyclization of N-aryl-N-(prop-2-yn-1-yl)benzenesulfonamide for the synthesis of 3-bromo-1,2-dihydroquinoline

被引：16

作者：

Yang, Min ^{[1
]}

Hu, Xin ^{[1
]}

Ouyang, Banlai ^{[2
]}

Xie, Wenlin ^{[3
]}

Liu, Jin-Biao ^{[4
]}

机构：

[1] Gannan Med Univ, Dept Forens Sci, 1 Yixueyuan Rd, Ganzhou 341000, Jiangxi, Peoples R China

[2] Nanchang Normal Univ, Dept Chem, Nanchang 330032, Jiangxi, Peoples R China

[3] Hunan Univ Sci & Technol, Sch Chem & Chem Engn, Xiangtan 411201, Hunan, Peoples R China

[4] Jiangxi Univ Sci & Technol, Dept Chem, 86 Hongqi Rd, Ganzhou 341000, Peoples R China

来源：

TETRAHEDRON | 2019年 / 75卷 / 25期

关键词：

N-aryl-N-(Prop-2-yn-1-yl) benzenesulfonamide; 3-Bromo-1,2-dihydroquinoline; Radical addition; 6-endo-trig cyclization; QUINOLINE N-OXIDES; SUBSTITUTED QUINOLINES; 1,2-DIHYDROQUINOLINE DERIVATIVES; ELECTROPHILIC CYCLIZATION; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; COUPLING REACTIONS; ACTIVATED ALKYNES; METAL; BROMINATION;

D O I：

10.1016/j.tet.2019.05.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this work, we described a new synthetic route of 3-bromo-1,2-dihydroquinoline derivatives based on the TBAB/Oxone-mediated radical 6-endo-trig ortho-cyclization of 2-alkynylbenzamide. The reaction proceeded smoothly with moderate functional group tolerance and high reaction efficiency. It is believed that radical addition, 6-endo-dig cyclization, and oxidation are all involved in the reaction processes. Furthermore, we successfully demonstrated the usability of these derivatives in further functionalization. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：3516 / 3522

页数：7

共 2 条

[1] The synthesis, crystal structure and Hirshfeld surface analysis of the thiophene derivatives 5-(phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]phenyl}-N-(prop-2-yn-1-yl)benzenesulfonamide
Madhan, S.
NizamMohideen, M.
Pavunkumar, Vinayagam
MohanaKrishnan, Arasambattu K.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2023, 79 : 521 - +
[2] CHIRAL SYNTHESIS OF 6,7-BENZOMORPHANS - SYNTHESIS OF (-)1(S),2(S),4(R),6(R)-1,2,3,4,5,6-HEXAHYDRO-2,6-METHANO-8-METHOXY-1,3,4,6-TETRAMETHYL-3-BENZAZOCINE THROUGH THE CHROMIUM HEXACARBONYL MEDIATED CYCLIZATION OF 1(S),1'(R)-1,2-DIHYDRO-7-METHOXY-1,4-DIMETHYL-1-(N-METHYL-N-TRIFLUOROACETAMIDO-1'-METHYLETHAN-2'-YL)NAPHTHALENE
SAINSBURY, M
MAHON, MF
WILLIAMS, CS
NAYLOR, A
SCOPES, DIC
TETRAHEDRON, 1991, 47 (24) : 4195 - 4210

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