Methanol as a Formylating Agent in Nitrogen Heterocycles

Author(s):  
Zhengbao Xu ◽  
Lizhi Zhang

A radical mediated C-H direct formylation of N-heteroarenes with methanol is reported. The reaction features a novel iron-catalyzed Minisci oxidative coupling process using commercially available methanol as a formylated reagent....

2019 ◽  
Vol 10 (40) ◽  
pp. 9265-9269 ◽  
Author(s):  
Jonathan M. Shikora ◽  
Chanchamnan Um ◽  
Zainab M. Khoder ◽  
Sherry R. Chemler

The oxidative coupling of alkyltrifluoroborates with heteroatom-tethered vinylarenes leads to a broad range of saturated oxygen and nitrogen heterocycles.


Author(s):  
Jiaoyang Wang ◽  
Danfeng Wang ◽  
Xiaofeng Tong

A MnO2-promoted oxidative coupling process between N,N-disubstituted hydrazine and boronic ester is reported. 1,1-Diazene species is firstly generated on oxidation of hydrazine substrate in the presence of MnO2 and then...


2007 ◽  
Vol 41 (20) ◽  
pp. 7073-7079 ◽  
Author(s):  
Salehe Ghasempur ◽  
Seyed-Fakhreddin Torabi ◽  
Seyed-Omid Ranaei-Siadat ◽  
Mehdi Jalali-Heravi ◽  
Nasser Ghaemi ◽  
...  

2009 ◽  
Vol 64 (6) ◽  
pp. 747-755 ◽  
Author(s):  
Christoph Heichert ◽  
Horst Hartmann

The reaction of aniline (AH2) with an oxidizing agent in acidic solution gives rise to the formation of a mixture of products containing, besides a variety of oligoanilines named as Aniline Black or Polyaniline, Mauvein as a deeply purple phenazine derivative. Although this Mauvein synthesis was developed by W.H. Perkin more than 150 years ago and has opened the era of industrial dyestuff chemistry, the detailed mechanism of this reaction has remained rather unclear until today. The elucidation of the mechanism of the Mauvein formation as an oxidative coupling process of AH2 is hindered by the fact that several different types of coupling reactions occur simultaneously. Among them the C,N-coupling reaction is the most important one and responsible for the formation of Polyaniline and Mauvein. It gives rise to the formation of, e. g. 2 different aniline dimers, 7 trimers and more than 20 tetramers including Mauvein as one representative of these tetramers. In the present study, the oxidative coupling of a mixture of AH2 and 4-amino-4`-(N-anilino)-diphenylamine (TaH2) as one of the aniline trimers was studied in more detail. The reaction leads to the formation of Mauvein in satisfactory yields and, after some manipulations, widely free of byproducts. By using simple aniline derivatives as co-reagents in the oxidative coupling with TaH2, the reaction can be extended to the synthesis of different Mauvein derivatives most of which have been unknown to date.


2019 ◽  
Vol 151 ◽  
pp. 56-69 ◽  
Author(s):  
Hamid Reza Godini ◽  
Mohammadreza Azadi ◽  
Alberto Penteado ◽  
Mohammadali Khadivi ◽  
Günter Wozny ◽  
...  

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1981-1990
Author(s):  
Mookda Pattarawarapan ◽  
Chuthamat Duangkamol ◽  
Wong Phakhodee

A convenient oxidative cyclodesulfurization method toward the synthesis of benzofused nitrogen heterocycles using inexpensive and readily available potassium periodate as an oxidant was developed. Upon treating isothiocyanates with ortho-substituted anilines bearing N,N-, N,O-, and N,S-bis-nucleophiles, followed by an intramolecular cyclization of the in situ generated monothioureas, substituted 2-aminobenzazole series were rapidly accessible in good to excellent yields. The protocol can accommodate various substituents on both substrates while allowing more efficient, greener, and operational simpler process relative to other oxidative coupling reactions. Tetracyclic quinazolinone derivatives were also afforded in high yields in a single preparative step and chromatography-free.


2018 ◽  
Vol 90 (9) ◽  
pp. 1135-1136
Author(s):  
H. R. Godini ◽  
A. Penteado ◽  
M. Khadivi ◽  
M. Azadi ◽  
T. Karsten ◽  
...  

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