A practical and mild chlorination of fused heterocyclic N-oxides

被引：34

作者：

Wang, Dong ^{[1
]}

Jia, Hailing ^{[2
]}

Wang, Wuchang ^{[2
]}

Wang, Zhe ^{[1
]}

机构：

[1] Longwood Biopharmaceut Co Ltd, Tianjin Int Joint Acad Biomed, Tianjin 300457, Peoples R China

[2] Nankai Univ, Sch Med, Tianjin 300071, Peoples R China

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 51期

关键词：

Chlorination; N-Oxides; Vilsmeier reagent; Quinoline; Isoquinoline; INHIBITORS; QUINOLINES; CONVERSION;

D O I：

10.1016/j.tetlet.2014.11.005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：7130 / 7132

页数：3

共 50 条

[31] A MILD DEOXYGENATION OF HETEROAROMATIC N-OXIDES WITH DIPHOSPHORUS TETRAIODIDE
SUZUKI, H
SATO, N
OSUKA, A
CHEMISTRY LETTERS, 1980, (04) : 459 - 460
[32] SYNTHESIS AND STUDIES ON N-OXIDES OF HETEROCYCLIC COMPOUNDS .1. N-OXIDES OF MORPHINE, TETRAHYDRO-ISOQUINOLINE AND QUINOLINE
KHALETSKII, AM
PESIN, VG
TSIN, C
ZHURNAL OBSHCHEI KHIMII, 1958, 28 (09): : 2348 - 2355
[33] A mild deoxygenation of heteroaromatic N-oxides by formamidinesulfinic acid
Balicki, R
Chmielowiec, U
MONATSHEFTE FUR CHEMIE, 2000, 131 (10): : 1105 - 1107
[34] An Improved Rapid and Mild Deoxygenation of Amine N-oxides
Rajesh, Y. B. R. D.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (02) : 486 - 491
[35] A Mild Deoxygenation of Heteroaromatic N-Oxides by Formamidinesulfinic Acid
Roman Balicki
Urszula Chmielowiec
Monatshefte für Chemie / Chemical Monthly, 2000, 131 : 1105 - 1107
[36] HETEROCYCLIC FLUORINE COMPOUNDS .5. FLUOROPYRIDINE OXIDES AND FLUOROQUINOLINE N-OXIDES
BELLAS, M
SUSCHITZKY, H
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (AUG): : 4007 - &
[37] BENZOATO-COPPER(II) COMPLEXES WITH HETEROCYCLIC N-OXIDES
KRATSMAR.J
MELNIK, M
ZEITSCHRIFT FUR NATURFORSCHUNG PART B-CHEMIE BIOCHEMIE BIOPHYSIK BIOLOGIE UND VERWANDTEN GEBIETE, 1969, B 24 (11): : 1479 - &
[38] THE MICROBIAL MUTAGENICITY AND TOXICITY OF NEWLY SYNTHESIZED HETEROCYCLIC N-OXIDES
ALMOSSAWI, MAJ
SALEM, AA
SALAMA, M
ANANI, A
MUTATION RESEARCH, 1982, 97 (03): : 165 - 165
[39] Practical metalation-heteroarylation of azine N-oxides
Gosselin, Francis
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[40] Synthesis of Benzimidazoles condensed with, or linked to, nitroxides or heterocyclic N-oxides
Bognar, Balazs
Kalai, Tamas
Hideg, Kalman
SYNTHESIS-STUTTGART, 2008, (15): : 2439 - 2445

← 1 2 3 4 5 →