Divergent Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines via Reagent-Controlled Cleavage of the C-N or C-C Azirine Bond in 2-Pyridylazirines

被引：4

作者：

Agafonova, Anastasiya V. ^{[1
]}

Golubev, Artem A. ^{[1
]}

Smetanin, Ilia A. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Spiridonova, Dar'ya V. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 39期

基金：

俄罗斯科学基金会;

关键词：

BIOLOGICAL EVALUATION; FLUORESCENT-PROBE; DERIVATIVES; DESIGN;

D O I：

10.1021/acs.orglett.3c02696

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The three-membered ring in 2-(2-pyridyl)azirine-2-carboxylic esters and thioesters can undergo selective cleavage of either the N-C2 bond under copper(II) catalysis or the C-C bond under the action of HCl to provide isomeric azirine ring expansion products of pyrazolo[1,5-a]pyridine or imidazo[1,5-a]pyridine series, respectively. Mild catalytic reaction conditions for the formation of pyrazolopyridines make it possible to obtain them directly from 4-bromoisoxazoles by a one-pot, three-stage procedure without isolating the intermediate 2-bromoazirines and 2-(2-pyridyl)azirines.

引用

页码：7165 / 7169

页数：5

共 50 条

[1] Divergent and Regioselective Synthesis of Pyrazolo[1,5-a]pyridines and Imidazo[1,5-a]pyridines
Mennie, Katrina M.
Reutershan, Michael H.
White, Catherine
Adams, Bruce
Becker, Bridget
Deng, James
Katz, Jason D.
LaBlue, Elisabeth
Margrey, Kaila
Sauri, Josep
ORGANIC LETTERS, 2021, 23 (12) : 4694 - 4698
[2] Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines
Zeng, Kui
Ye, Jin
Meng, Xintong
Dechert, Sebastian
Simon, Martin
Gong, Shuaiyu
Mata, Ricardo A.
Zhang, Kai
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (29)
[3] Copper-mediated synthesis of pyrazolo[1,5-a]-pyridines through oxidative linkage of C-C/N-N bonds
Mohan, Darapaneni Chandra
Ravi, Chitrakar
Rao, Sadu Nageswara
Adimurthy, Subbarayappa
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) : 3556 - 3560
[4] New approach toward the synthesis of deuterated pyrazolo[1,5-a] pyridines and 1,2,4-triazolo[1,5-a] pyridines
Vorob'ev, Aleksey Yu.
Supranovich, Vyacheslav I.
Borodkin, Gennady I.
Shubin, Vyacheslav G.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2017, 13 : 800 - 805
[5] NOVEL SYNTHESIS OF PYRAZOLO=1,5-A'PYRIDINES VIA YLIDE INTERMEDIATES
TAMURA, Y
TSUJIMOT.N
IKEDA, M
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (07): : 310 - &
[6] SYNTHESIS OF 2,6-DISUBSTITUTED PYRIDINES BY LITHIATION OF PYRAZOLO[1,5-A] PYRIDINES
MIYASHITA, A
SATO, Y
WATANABE, S
TANJI, K
HIGASHINO, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 1995, 43 (01) : 174 - 176
[7] Synthesis and Mechanistic Investigation of Bipyrazolo[1,5-a]pyridines via Palladium-Catalyzed Cross-Dehydrogenative Coupling of Pyrazolo[1,5-a]pyridines
Hsiao, Pu-Yen
Chang, Rong
Sue, Andrew C. -H.
Chu, Jean -Ho
Liao, Guan-Wei
Lee, Yi-Hsin
Huang, Jui-Yang
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (15): : 9851 - 9863
[8] SYNTHESIS OF PYRAZOLO[1,5-A]PYRIDINES AND PYRAZOLO[1,5-C]PYRIMIDINES BY REACTION OF HETEROCYCLIC AMIDRAZONES WITH 1,3-DICARBONYL COMPOUNDS
KOCKRITZ, P
RIEMER, B
MICHLER, A
HASSOUN, A
LIEBSCHER, J
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (05) : 1157 - 1160
[9] Anomeric Stereoauxiliary Cleavage of the C-N Bond of d-Glucosamine for the Preparation of Imidazo[1,5-a]pyridines (vol 28, e202200648, 2022)
Zeng, Kui
Ye, Jin
Meng, Xintong
Dechert, Sebastian
Simon, Martin
Gong, Shuaiyu
Mata, Ricardo A.
Zhang, Kai
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (48)
[10] Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes
Aksenov, Dmitrii A.
Arutiunov, Nikolai A.
Maliuga, Vladimir V.
Aksenov, Alexander, V
Rubin, Michael
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 2903 - 2910

← 1 2 3 4 5 →