Study of 1,3-dipolar cycloaddition of amino-acid azomethines and Juglone

被引:1
作者
Syngaevsky, Vadym [1 ]
Karkhut, Andrew [1 ]
Polovkovych, Sviatoslav [1 ]
Gzella, Andrzej [2 ]
Lesyk, Roman [3 ,4 ]
Novikov, Volodymyr [1 ]
机构
[1] Lviv Polytech Natl Univ, Dept Technol Biol Act Subst Pharm & Biotechnol, Lvov, Ukraine
[2] Poznan Univ Med Sci, Dept Organ Chem, Poznan, Poland
[3] Danylo Halytsky Lviv Natl Med Univ, Dept Pharmaceut Organ & Bioorgan Chem, Pekarska 69, UA-79010 Lvov, Ukraine
[4] Univ Informat Technol & Management Rzeszow, Fac Med, Dept Publ Hlth Dietet & Lifestyle Disorders, Rzeszow, Poland
关键词
13-cycloaddition; amino acids; azomethines; Juglone; X-ray; PROTEIN-KINASE-C; X=Y-ZH SYSTEMS; PYRROLIDINE DERIVATIVES; POTENTIAL 1,3-DIPOLES; TOPOISOMERASE-I; INHIBITOR; YLIDES; ATORVASTATIN; STRATEGY; PROLINE;
D O I
10.1080/00397911.2020.1795880
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel 2,3,4,9-tetrahydro- and 4,9-dihydro-1H-benzo[f]isoindole derivatives were synthesized from Juglone and amino-acid azomethines in 74-85% yields via 1,3-dipolar cycloaddition. The stereo- and regioselectivity of cycloaddition was confirmed by NMR spectra and single-crystal X-ray diffraction analysis.
引用
收藏
页码:3165 / 3173
页数:9
相关论文
共 52 条
[1]   Silver-mediated synthesis of heterocycles [J].
Alvarez-Corral, Miriam ;
Munoz-Dorado, Manuel ;
Rodirguez-Garcia, Ignacio .
CHEMICAL REVIEWS, 2008, 108 (08) :3174-3198
[2]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .8. PYRROLIDINES AND DELTA-5-PYRROLINES (3,7-DIAZABICYCLO[3.3.0]OCTENES) FROM THE REACTION OF IMINES OF ALPHA-AMINO-ACIDS AND THEIR ESTERS WITH CYCLIC DIPOLAROPHILES - MECHANISM OF RACEMIZATION OF ALPHA-AMINO-ACIDS AND THEIR ESTERS IN THE PRESENCE OF ALDEHYDESN [J].
AMORNRAKSA, K ;
GRIGG, R ;
GUNARATNE, HQN ;
KEMP, J ;
SRIDHARAN, V .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (10) :2285-2296
[3]   Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].
Bellina, Fabio ;
Rossi, Renzo .
TETRAHEDRON, 2006, 62 (31) :7213-7256
[4]   Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics [J].
Bhardwaj, Varun ;
Gumber, Divya ;
Abbot, Vikrant ;
Dhiman, Saurabh ;
Sharma, Poonam .
RSC ADVANCES, 2015, 5 (20) :15233-15266
[5]   New pyrrole derivatives as antimycobacterial agents analogs of BM212 [J].
Biava, M ;
Fioravanti, R ;
Porretta, GC ;
Deidda, D ;
Maullu, C ;
Pompei, R .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (20) :2983-2988
[6]   Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions [J].
Boger, DL ;
Boyce, CW ;
Labroli, MA ;
Sehon, CA ;
Jin, Q .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :54-62
[7]   Catalytic asymmetric [3+2] cycloaddition of azomethine ylides. Development of a versatile stepwise, three-component reaction for diversity-oriented synthesis [J].
Chen, C ;
Li, XD ;
Schreiber, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (34) :10174-10175
[8]   FACILE THREE-COMPONENT SYNTHESIS OF SPIROOXINDOLEPYRROLOLINE RING SYSTEMS VIA 1,3-DIPOLAR CYCLOADDITION WITH 1,4-NAPHTHOQUINONE [J].
Chen, Hua ;
Wang, Shun-Yi ;
Xu, Xiao-Ping ;
Ji, Shun-Jun .
SYNTHETIC COMMUNICATIONS, 2011, 41 (22) :3280-3288
[9]  
Chong PH, 1997, PHARMACOTHERAPY, V17, P1157
[10]   Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].
Coldham, I ;
Hufton, R .
CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809