Synthesis of 5-[4-(Arylsulfanyl)phenyl]-2,2'-bipyridines Using Aryne Intermediates

被引：0

作者：

Starnovskaya, E. S. ^{[1
,2
]}

Krinochkin, A. P. ^{[1
,2
]}

Rybakova, S. S. ^{[1
]}

Muzyka, A. L. ^{[1
]}

Slepukhin, P. A. ^{[1
,2
]}

Kopchuk, D. S. ^{[1
,2
]}

Zyryanov, G. V. ^{[1
,2
]}

Chupakhin, O. N. ^{[1
,2
]}

机构：

[1] Ural Fed Univ, Ekaterinburg 620002, Russia

[2] Russian Acad Sci, Ural Branch, Postovsky Inst Organ Synth, Ekaterinburg 620219, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2023年 / 93卷 / 07期

基金：

俄罗斯科学基金会;

关键词：

1,2,4-triazines; 2,2'-bipyridines; 1,2-dehydrobenzene; S-arylation; aza-Diels-Alder reaction; 1,2,4-TRIAZINES; DESIGN;

D O I：

10.1134/S107036322307006X

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

convenient method for the preparation of 5-aryl-2,2'-bipyridines with para-arylsulfanyl group in an aromatic substituent was proposed. The synthesis was performed using in situ generated aryne intermediates without the use of complex experimental procedures and expensive reagents/catalysts. The structure of one product was confirmed by XRD data. This approach is a new variant for the preparation of 5-aryl-2,2'-bipyridines with an extended conjugation system.

引用

页码：1680 / 1686

页数：7

共 50 条

[1] Synthesis of 5-[4-(Arylsulfanyl)phenyl]-2,2′-bipyridines Using Aryne Intermediates
E. S. Starnovskaya
A. P. Krinochkin
S. S. Rybakova
A. L. Muzyka
P. A. Slepukhin
D. S. Kopchuk
G. V. Zyryanov
O. N. Chupakhin
Russian Journal of General Chemistry, 2023, 93 : 1680 - 1686
[2] Disulfide-Functionalized 3-, 4-, 5-, and 6-substituted 2,2′-bipyridines and their ruthenium complexes
Panetta, CA
Kumpaty, HJ
Heimer, NE
Leavy, MC
Hussey, CL
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03): : 1015 - 1021
[3] Functionalization of 2,2'-Bipyridines in Their 4 and 5 Positions. Synthesis of 5-Ethynyl-2,2'-bipyridine
Pohn, J.
Schmohel, E.
Balzani, V.
Synthesis, (03):
[4] Functionalization of 2,2′-bipyridines in their 4 and 5 positions.: Synthesis of 5-ethynyl-2,2′-bipyridine
Polin, J
Schmohel, E
Balzani, V
SYNTHESIS-STUTTGART, 1998, (03): : 321 - 324
[5] Synthesis and mesomorphic properties of 5-[4-(alkyloxy)phenyl]-2-{4′-[(S)-2-methylbutyl]phenyl}pyrimidine
Park, SU
Lee, CJ
Han, AF
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (07) : 1033 - 1034
[6] Synthesis of Unsymmetrical 5,5'-Disubstituted 2,2'-Bipyridines
J Org Chem, 9 (3013):
[7] SYNTHESIS OF UNSYMMETRICALLY 4-SUBSTITUTED 2,2'-BIPYRIDINES
KELLYBASETTI, BM
KRODKIEWSKA, I
SASSE, WHF
SAVAGE, GP
SIMPSON, GW
TETRAHEDRON LETTERS, 1995, 36 (02) : 327 - 330
[8] THE SYNTHESIS OF SOME 4,4'-DISUBSTITUTED 2,2'-BIPYRIDINES
MAERKER, G
CASE, FH
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (11) : 2745 - 2748
[9] 4-[4-(Methylsulfanyl)phenyl]-6-phenyl-2,2′-bipyridine
Polson, Matthew I. J.
Scandola, Franco
Steel, Peter J.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O279 - U5131
[10] Synthesis of 5,5′-disubstituted 2,2′-bipyridines for modular chemistry
Henze, O
Lehmann, U
Schlüter, AD
SYNTHESIS-STUTTGART, 1999, (04): : 683 - 687

← 1 2 3 4 5 →