Efficient synthesis of n-oxide derivatives:: Substituted 2-(2-(Pyridyl-N-oxide) methylsulphinyl) benzimidazoles

被引：3

作者：

Ray, Purna C. ^{[1
]}

Mittapelli, Vasantha ^{[1
]}

Rohatgi, Amit ^{[1
]}

Tyagi, Om Dutt ^{[1
]}

机构：

[1] Matrix Labs Ltd, Jinnaram 502325, AP, India

来源：

SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 17期

关键词：

lansoprazole N-oxide; mCPBA; omeprazole N-oxide; pantoprazole; N-oxide; rabeprazole N-oxide;

D O I：

10.1080/00397910701470693

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Different substituted 2-chloromethylpyridyl derivatives (6a-d) were oxidized with mCPBA to give the respective 2-chloromethylpyridine-N-oxide derivatives (7a-d) at low temperature, which on condensation with 2-mercapto-1H-benzimidazole (8a-c) in the presence of aprotic solvents give the 2-[[(pyridin-2-yl-1-oxide) methyl]sulfanyl]-1H-benzimidazole (9a-d) in good yield. Finally, 9a-d oxidized with mCPBA in chlorinated solvent gives a mixture of 2-[[(pyridin-2-yl-1-oxide) methyl]sulfonyl]-1H-benzimidazole (3a-d, 10%) and 2-[[(pyridin-2-yl-1-oxide) methyl] sulfinyl]1H-benzimidazole (4a-d, 90%) derivatives.

引用

页码：2861 / 2868

页数：8

共 50 条

[31] SUBSTITUTED PYRIDINE N-OXIDE COMPLEXES OF COBALT(2) CHLORIDE
RAMASWAMY, HN
JONASSEN, HB
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1965, 27 (03): : 740 - +
[32] CYCLOADDITION OF 2,3,4,5-TETRAHYDROPYRIDINE N-OXIDE TO VINYL ETHERS - ENANTIOSELECTIVE SYNTHESIS OF 2-(N-BENZYLPIPERIDIN-2-YL)ETHANOL
CARRUTHERS, W
COGGINS, P
WESTON, JB
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (02) : 117 - 118
[33] N,N′-Bis[2-(2-pyridyl)ethyl]dithiooxamide
Cui, JZ
Zhang, D
Pan, SW
Cheng, P
Liao, DZ
Wang, GL
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O1913 - O1915
[34] Synthesis and deprotonation of 2-(pyridyl)phenols and 2-(pyridyl)anilines
Rebstock, AS
Mongin, F
Trécourt, F
Quéguiner, G
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (17) : 3064 - 3068
[35] SPECTROPHOTOMETRIC STUDY OF THE PROPERTIES OF CERTAIN AZOCOMPOUNDS BASED ON PYRIDYL-N-OXIDE
PISICHENKO, GM
KOLESNIKOVA, AS
DOMINOVA, IG
JOURNAL OF ANALYTICAL CHEMISTRY OF THE USSR, 1986, 41 (04): : 502 - 510
[36] THERMAL DECOMPOSITION OF SOME PYRIDINE N-OXIDE AND SUBSTITUTED PYRIDINE N-OXIDE COMPLEXES OF MANGANESE(2), COBALT(2), NICKEL(2), AND ZINC(2) HALIDES
BROWN, DH
KENYON, D
SHARP, DWA
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1969, (10): : 1474 - &
[37] SYNTHESIS OF N-(ALKYLOXY)PYRIDINE-2(1H)-THIONES - ALKYLATIONS OF THE AMBIDENT NUCLEOPHILE PYRIDINE-2(1H)-THIONE N-OXIDE AND ATTEMPTED ISOMERIZATIONS OF 2-(ALKYLTHIO)PYRIDINE N-OXIDE
HAY, BP
BECKWITH, ALJ
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (18): : 4330 - 4334
[38] Structure of substituted 2-(phenoxy)benzimidazoles
Pavlova, I. S.
Pervova, I. G.
Lipunova, G. N.
Novikova, R. K.
Slepukhin, P. A.
Lipunov, I. N.
CRYSTALLOGRAPHY REPORTS, 2013, 58 (02) : 271 - 274
[39] 2-Substituted Benzimidazole Synthesis in Dry Medium Mediated by Pyridine N-oxide
Bratulescu, George
REVISTA DE CHIMIE, 2018, 69 (12): : 3569 - 3572
[40] Structure of substituted 2-(phenoxy)benzimidazoles
I. S. Pavlova
I. G. Pervova
G. N. Lipunova
R. K. Novikova
P. A. Slepukhin
I. N. Lipunov
Crystallography Reports, 2013, 58 : 271 - 274

← 1 2 3 4 5 →