SNH- and SNipso-Arylamination of 1,3,7-Triazapyrenes

被引:21
作者
Borovlev, Ivan [1 ]
Demidov, Oleg [1 ]
Saigakova, Nadezhda [1 ]
Amangasieva, Gulminat [1 ]
机构
[1] North Caucasus Fed Univ, Dept Chem, Stavropol 355029, Russia
关键词
Amination; Aromatic substitution; Nucleophilic substitution; Nitrogen heterocycles; Polycycles; NUCLEOPHILIC AROMATIC-SUBSTITUTION; PALLADIUM-CATALYZED AMINATION; OXIDATIVE ALKYLAMINATION; 7-ALKYL-1,3,7-TRIAZAPYRENIUM SALTS; HYDROGEN; NITROQUINOLINES; HYDROXYLATION; ALKOXYLATION; ANNELATION; ACIDITIES;
D O I
10.1002/ejoc.201402891
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ability of the oxidative arylamination process to derivatize electron-deficient 1,3,7-triazapyrenes has been investigated. These triazapyrenes react with a wide range of sodium aryl(hetaryl) amides to give access to the corresponding 6-aryl(hetaryl)amino-1,3,7-triazapyrenes in moderate to good yields. The reaction of 6,8-dialkoxy-1,3,7-triazapyrene with sodium arylamides gives rise to 6,8-bis(arylamino)-1,3,7-triazapyrenes or 6-methoxy-8-arylamino-1,3,7-triazapyrenes, depending on the reaction conditions.
引用
收藏
页码:7675 / 7683
页数:9
相关论文
共 54 条
[41]  
Matern A. I., 2007, RUSS CHEM REV, V76, P23, DOI [DOI 10.1070/RC2007V076N01ABEH003647, DOI 10.1070/RC2007v076n01ABEH003647]
[42]   Synthesis of nitro N,N′-dipyridinylamines via oxidative nucleophilic substitution of hydrogen [J].
Patriciu, Oana-Irina ;
Pillard, Christelle ;
Finaru, Adriana-Luminita ;
Sandulescu, Loan ;
Guillaumet, Gerald .
SYNTHESIS-STUTTGART, 2007, 24 (24) :3868-3876
[43]   1,2,4-TRIAZINES .4. SYNTHESIS AND CHARACTERIZATION OF 1,2,4-TRIAZINE N-OXIDES [J].
PAUDLER, WW ;
CHEN, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (06) :787-&
[44]   Palladium-Catalysed Amination of Aryl- and Heteroaryl Halides Using tertButyl Tetraisopropylphosphorodiamidite as an Easily Accessible and Air-Stable Ligand [J].
Roiban, Gheorghe-Doru ;
Mehler, Gerlinde ;
Reetz, Manfred T. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) :2070-2076
[45]   Direct Amination of 1-substituted 3,5-dinitrobenzenes by 1,1,1-trimethylhydrazinium iodide [J].
Rozhkov, VV ;
Shevelev, SA ;
Chervin, I ;
Mitchell, AR ;
Schmidt, RD .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2498-2501
[46]   Synthesis of Functionalized Pyridazin-3(2H)-ones via Bromine-Magnesium Exchange on Bromopyridazin-3(2H)-ones [J].
Ryabtsova, Oxana ;
Verhelst, Tom ;
Baeten, Mattijs ;
Velde, Christophe M. L. Vande ;
Maes, Bert U. W. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (24) :9440-9445
[47]  
Schaefer T., 2011, [No title captured], Patent No. [US 20110186821 A1, 20110186821]
[48]  
Shaefer T., 2010, W. O. Patent, Patent No. 2010031738
[49]   Biaryl phosphane ligands in palladium-catalyzed amination [J].
Surry, David S. ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (34) :6338-6361
[50]  
Surry S., 2008, ANGEW CHEM, V120, P6438