15N labeling and analysis of 13C-15N and 1H-15N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

被引:27
作者
Deev, Sergey L. [1 ,2 ]
Khalymbadzha, Igor A. [1 ]
Shestakova, Tatyana S. [1 ]
Charushin, Valery N. [1 ,2 ]
Chupakhin, Oleg N. [1 ,2 ]
机构
[1] Ural Fed Univ, 19 Mira St, Ekaterinburg 620002, Russia
[2] I Ya Postovsky Inst Organ Synth, 22 S Kovalevskoy St, Ekaterinburg 620219, Russia
基金
俄罗斯基础研究基金会;
关键词
AZIDE-TETRAZOLE EQUILIBRIUM; DIMROTH REARRANGEMENT; RING; TAUTOMERISM; SPECTROSCOPY; ALKYLATION; NITRATION; MECHANISM; PRODUCTS; HCNMBC;
D O I
10.1039/c9ra04825a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This review provides a generalization of effective examples of N-15 labeling followed by an analysis of C-13-N-15 (J(CN)) and H-1-N-15 (J(HN)) coupling constants in solution as a tool to study the structural aspects and pathways of chemical transformations (e.g., rearrangements and ring-chain tautomerisms) in monocyclic and fused nitrogen heterocycles. This approach allows us to significantly expand and supplement the scope of NMR techniques for heterocyclic compounds. Moreover, methods for the incorporation of N-15 atoms into the cores of various N-heterocycles have been collected in this work.
引用
收藏
页码:26856 / 26879
页数:24
相关论文
共 66 条
[1]   RING TRANSFORMATION EQUILIBRIUM (BOND SWITCH) IN THE 5-(2-AMINOVINYL)ISOTHIAZOLE SYSTEM VIA HYPERVALENT SULFURANE - SYNTHESIS, STRUCTURE DETERMINATION, AND KINETIC-STUDY [J].
AKIBA, KY ;
KASHIWAGI, K ;
OHYAMA, Y ;
YAMAMOTO, Y ;
OHKATA, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (09) :2721-2730
[2]   N-15-LABELLED 3-(DIMETHYLAMINO)-2,2-DIMETHYL-2H-AZIRINE FOR MECHANISTIC STUDIES OF REACTIONS WITH NH-ACIDIC HETEROCYCLES [J].
AMETAMEY, SM ;
HOLLENSTEIN, R ;
HEIMGARTNER, H .
HELVETICA CHIMICA ACTA, 1988, 71 (03) :521-530
[3]  
[Anonymous], 2013, Tautomerism: Methods and Theories, DOI DOI 10.1002/9783527658824.CH5
[4]   A NEW ROUTE TO N-15-LABELED, N-ALKYL, AND N-AMINO NUCLEOSIDES VIA N-NITRATION OF URIDINES AND INOSINES [J].
ARIZA, X ;
BOU, V ;
VILARRASA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (13) :3665-3673
[5]   Unexpected Observation of the Dimroth Rearrangement in the Ribosylation of 4-Aminopyrimidines [J].
Baiazitov, Ramil Y. ;
Sydorenko, Nadiya ;
Ren, Hongyu ;
Moon, Young-Choon .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11) :5881-5889
[6]   An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles [J].
Baumann, Marcus ;
Baxendale, Ian R. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 :2265-2319
[7]  
BAX A, 1994, METHOD ENZYMOL, V239, P79
[8]   THERMAL REARRANGEMENT OF 1,4-DINITROIMIDAZOLE TO 2,4-DINITROIMIDAZOLE - CHARACTERIZATION AND INVESTIGATION OF THE MECHANISM BY MASS-SPECTROMETRY AND ISOTOPE LABELING [J].
BULUSU, S ;
DAMAVARAPU, R ;
AUTERA, JR ;
BEHRENS, R ;
MINIER, LM ;
VILLANUEVA, J ;
JAYASURIYA, K ;
AXENROD, T .
JOURNAL OF PHYSICAL CHEMISTRY, 1995, 99 (14) :5009-5015
[9]   Synthesis and antitumor activities of 1,2,3-triazines and their benzo- and heterofused derivatives [J].
Cascioferro, Stella ;
Parrino, Barbara ;
Spano, Virginia ;
Carbone, Anna ;
Montalbano, Alessandra ;
Barraja, Paola ;
Diana, Patrizia ;
Cirrincione, Girolamo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 142 :74-86
[10]  
Cavanagh J, 2007, PROTEIN NMR SPECTROSCOPY: PRINCIPLES AND PRACTICE, 2ND EDITION, P1