Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters

被引:1
作者
Gucma, Miroslaw [1 ]
Golebiewski, W. Marek [1 ]
Zelechowski, Krzysztof [1 ]
Krawczyk, Maria [1 ]
机构
[1] Inst Ind Organ Chem, Annopol 6, PL-3236 Warsaw, Poland
关键词
dipolar cycloaddition; abietates; site selectivity; NMR spectroscopy; BIOLOGICAL EVALUATION; DERIVATIVES;
D O I
10.2298/JSC180517018G
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[2+3] Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.
引用
收藏
页码:1073 / 1081
页数:9
相关论文
共 23 条
[1]   1,3-DIPOLAR CYCLOADDITIONS .70. ADDITIONS OF BENZONITRILE OXIDE TO OLEFINIC AND ACETYLENIC DIPOLAROPHILES [J].
BAST, K ;
CHRISTL, M ;
HUISGEN, R ;
MACK, W ;
SUSTMANN, R .
CHEMISCHE BERICHTE-RECUEIL, 1973, 106 (10) :3258-3274
[2]   Thiophosphoramides as cooperative catalysts for copper-catalyzed arylation of carboxylates with diaryliodonium salts [J].
Bhattarai, Bijay ;
Tay, Jia-Hui ;
Nagorny, Pavel .
CHEMICAL COMMUNICATIONS, 2015, 51 (25) :5398-5401
[3]  
Caramella P., 1984, 1 3 DIPOLAR CYCLOADD, P177
[4]   DERIVATIVES OF TETRAHYDRO-2H-PYRIDINE FROM PHOTO-REARRANGED CYCLOADDUCTS OF NITRILE OXIDES [J].
FISERA, L ;
ONDRUS, V ;
TIMPE, HJ .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (02) :512-523
[5]   Intramolecular 1,3-dipolar nitrone and nitrile oxide cycloaddition of 2-and 4-O-allyl and propargyl glucose derivatives:: a versatile approach to chiral cyclic ether fused isoxazolidines, isoxazolines and isoxazoles [J].
Ghorai, S ;
Mukhopadhyay, R ;
Kundu, AP ;
Bhattacharjya, A .
TETRAHEDRON, 2005, 61 (12) :2999-3012
[6]   Synthesis and biological evaluation of dehydroabietic acid derivatives [J].
Gonzalez, Miguel A. ;
Perez-Guaita, David ;
Correa-Royero, Julieth ;
Zapata, Bibiana ;
Agudelo, Lee ;
Mesa-Arango, Ana ;
Betancur-Galvis, Liliana .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (02) :811-816
[7]   Synthesis and biological evaluation of abietic acid derivatives [J].
Gonzalez, Miguel A. ;
Correa-Royero, Julieth ;
Agudelo, Lee ;
Mesa, Ana ;
Betancur-Galvis, Liliana .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (06) :2468-2472
[8]   Studies on [2+3] cycloaddition reaction of nitrile oxides to linear dipolarophiles bearing multiple double bonds [J].
Gucma, Miroslaw ;
Golebiewski, W. Marek ;
Michalczyk, Alicja Katarzyna .
MONATSHEFTE FUR CHEMIE, 2016, 147 (10) :1809-1818
[9]   NMR Studies on 1,3-Dipolar Cycloaddition of Nitrile Oxides to Norbornenes [J].
Gucma, Miroslaw ;
Golebiewski, W. Marek ;
Krawczyk, Maria .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2013, 24 (05) :805-+
[10]   ORIGIN OF REACTIVITY, REGIOSELECTIVITY, AND PERISELECTIVITY IN 1,3-DIPOLAR CYCLOADDITIONS [J].
HOUK, KN ;
SIMS, J ;
WATTS, CR ;
LUSKUS, LJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) :7301-7315