Use of Formic Acid as a CO Surrogate for the Reduction of Nitroarenes in the Presence of Dienes: A Two-Step Synthesis of N-Arylpyrroles via 1,2-Oxazines

被引：1

作者：

Fouad, Manar Ahmed ^{[1
,2
]}

Ferretti, Francesco ^{[1
]}

Galie, Simone ^{[1
]}

Ragaini, Fabio ^{[1
]}

机构：

[1] Univ Milan, Dept Chem, Via C Golgi 19, I-20133 Milan, Italy

[2] Alexandria Univ, Fac Sci, Chem Dept, POB 426, Alexandria 21321, Egypt

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 26卷 / 38期

关键词：

homogeneous catalysis; formic acid; nitroarenes; nitrogen heterocycles; CO surrogates; DIELS-ALDER REACTION; CATALYZED ELECTROPHILIC AMINATION; ORGANIC NITRO-COMPOUNDS; OXYGEN-ATOM-TRANSFER; CARBON-MONOXIDE; PHENYL FORMATE; UNFUNCTIONALIZED DIENES; CARBONYLATION REACTIONS; CYCLIZATION; NITROSTYRENES;

D O I：

10.1002/ejoc.202300809

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Formic acid, activated by acetic anhydride and a base, was employed as a CO surrogate to deoxygenate nitroarenes to nitrosoarenes, a reaction catalyzed by a palladium/phenanthroline complex in the homogeneous phase. Nitrosoarenes were trapped by conjugated dienes to give 3,6-dihydro-2H-[1,2]-oxazines. The latter were then transformed into N-arylpyrroles employing CuCl as the catalyst. The reaction was designed to give the best results for pyrroles lacking any substituent in the 2 and 5 positions, which are difficult to produce employing most pyrrole syntheses.

引用

页数：9

共 111 条

[21] Dongbo Z., 2007, EUR J ORG CHEM, V2007, P4431
[22] Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles (vol 2017, pg 1902, 2017)
EL-Atawy, Mohamed A.
Ferretti, Francesco
Ragaini, Fabio
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (30) : 4968 - 4968
[23] Synthesis of 3,6-Dihydro-2H-[1,2]-Oxazines from Nitroarenes and Conjugated Dienes, Catalyzed by Palladium/Phenanthroline Complexes and Employing Phenyl Formate as a CO Surrogate
EL-Atawy, Mohamed A.
Formenti, Dario
Ferretti, Francesco
Ragaini, Fabio
[J]. CHEMCATCHEM, 2018, 10 (20) : 4707 - 4717
[24] Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles
El-Atawy, Mohamed A.
Ferretti, Francesco
Ragaini, Fabio
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (14) : 1902 - 1910
[25] Recent advances in the synthesis of pyrroles by multicomponent reactions
Estevez, Veronica
Villacampa, Mercedes
Menendez, J. Carlos
[J]. CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) : 4633 - 4657
[26] Multicomponent reactions for the synthesis of pyrroles
Estevez, Veronica
Villacampa, Mercedes
Carlos Menendez, J.
[J]. CHEMICAL SOCIETY REVIEWS, 2010, 39 (11) : 4402 - 4421
[27] Effective Synthesis of 4-Quinolones by Reductive Cyclization of 2′-Nitrochalcones Using Formic Acid as a CO Surrogate
Ferretti, Francesco
Fouad, Manar Ahmed
Abbo, Cecilia
Ragaini, Fabio
[J]. MOLECULES, 2023, 28 (14):
[28] Synthesis of Indoles by Palladium-Catalyzed Reductive Cyclization of β-Nitrostyrenes with Phenyl Formate as a CO Surrogate
Ferretti, Francesco
Fouad, Manar Ahmed
Ragaini, Fabio
[J]. CATALYSTS, 2022, 12 (01)
[29] Transition Metal Catalyzed Reductive Cyclization Reactions of Nitroarenes and Nitroalkenes
Ferretti, Francesco
Ramadan, Doaa R.
Ragaini, Fabio
[J]. CHEMCATCHEM, 2019, 11 (18) : 4450 - 4488
[30] The reduction of organic nitro compounds by carbon monoxide as an effective strategy for the synthesis of N-heterocyclic compounds: a personal account
Ferretti, Francesco
Formenti, Dario
Ragaini, Fabio
[J]. RENDICONTI LINCEI-SCIENZE FISICHE E NATURALI, 2017, 28 : 97 - 115

← 1 2 3 4 5 6 7 8 9 10 →