Synthesis of novel functionalized dihydroimidazo[2,1-a] isoquinolines and dihydroimidazo[2,1-a] quinolines: single crystal X-ray studies of (Z)-methyl 2-(1-(benzo[d]thiazol-2-yl)-2-oxo-1,2-dihydroimidazo [2,1-a] isoquinolin-3 (10bH)-ylidene)acetate

被引:14
作者
Arab-Salmanabadi, Samira [1 ]
Dorvar, Marzieh [1 ]
Notash, Behrouz [2 ]
机构
[1] Islamic Azad Univ, Dept Chem, Shahr E Qods Branch, Tehran, Iran
[2] Shahid Beheshti Univ, Dept Chem, GC, Tehran 1983963113, Iran
关键词
Dihydroimidazo[2,1-a]isoquinoline; Dihydroimidazo[2,1-a]quinoline; Nitrogen heterocycles; Zwitterionic intermediate; Single crystal X-ray; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SATURATED HETEROCYCLES; ACTIVATED ACETYLENES; CATALYZED SYNTHESIS; EFFICIENT; OPTIMIZATION; INHIBITORS;
D O I
10.1016/j.tet.2014.12.076
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of novel functionalized dihydroimidazo[2,1-a]isoquinolines and dihydroimidazo[2,1-a] quinolines were synthesized via the reaction between isoquinoline or quinoline derivatives and dialkyl acetylenedicarboxylates in the presence of 2-aminobenzothiazole in excellent yields. These novel synthesized compounds were suitably characterized by elemental analysis, Mass spectroscopy, IR, H-1-NMR & C-13-NMR spectra. In addition the compound (Z)-methyl 2-(1-(benzo[d]thiazol-2-yl)-2-oxo-1,2-dihydroimidazo[2,1-a]isoquinolin-3(10bH)-ylidene)acetate was subjected to the single crystal X-ray diffraction studies. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1292 / 1296
页数:5
相关论文
共 42 条
[1]   Palladium catalyzed synthesis of 4-substituted-2-phenylimidazoles from N-propargyl-benzamidine [J].
Abbiati, Giorgio ;
Arcadi, Antonio ;
Canevaria, Valentina ;
Rossia, Elisabetta .
TETRAHEDRON LETTERS, 2007, 48 (48) :8491-8495
[2]   One-pot synthesis of 4,5-dihydro-1H-pyrrol-3-carboxamide derivatives via a four-component reaction [J].
Alizadeh, Abdolah ;
Rezvanian, Atieh ;
Zhu, Long-Guan .
TETRAHEDRON, 2008, 64 (02) :351-355
[3]   One-pot synthesis of 4-(alkylamino)-1-(arylsulfonyl)-3-benzoyl-1,5-dihydro-5-hydroxy-5-phenyl-2H-pyrrol-2-ones via a multicomponent reaction [J].
Alizadeh, Abdolah ;
Rezvanian, Atieh ;
Zhu, Long-Guan .
HELVETICA CHIMICA ACTA, 2007, 90 (12) :2414-2420
[4]   One-pot synthesis of arylsulfonamides and azetidine-2,4-diones via multicomponent reaction of an amine, an acetylenic compound, and an arylsuffonyl isocyanate [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh .
SYNTHESIS-STUTTGART, 2008, (11) :1747-1752
[5]   Synthesis of highly functionalized pyrrole derivatives via a four-component reaction of two primary Amines and diketene in the presence of nitrostyrene [J].
Alizadeh, Abdolali ;
Rezvanian, Atieh ;
Bijanzadeh, Hamid R. .
SYNTHESIS-STUTTGART, 2008, (05) :725-728
[6]   One-pot synthesis of spiro pyrroloimidazoles and 2-arylimidazoles from 1,2-diaza-1,3-butadienes and arylamidines [J].
Attanasi, Orazio A. ;
Giorgi, Gianluca ;
Favi, Glanfranco ;
Filippone, Paolino ;
Lillini, Samuele ;
Perrulli, Francesca R. ;
Santeisanio, Stefania .
SYNLETT, 2007, (11) :1691-1694
[7]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934
[8]   1-(3-cyanobenzylpiperidin-4-yl)-5-methyl-4-phenyl-1,3-dihydroimidazol-2-one:: A selective high-affinity antagonist for the human dopamine D4 receptor with excellent selectivity over ion channels [J].
Carling, RW ;
Moore, KW ;
Moyes, CR ;
Jones, EA ;
Bonner, K ;
Emms, F ;
Marwood, R ;
Patel, S ;
Patel, S ;
Fletcher, AE ;
Beer, M ;
Sohal, B ;
Pike, A ;
Leeson, PD .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (14) :2706-2715
[9]   Synthesis of axinohydantoins [J].
Carolina, A ;
Sosa, B ;
Yakushijin, K ;
Horne, DA .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4498-4500
[10]   aza-annulation of tetrahydroisoquinoline derived enamines:: Efficient and convergent routes to novel functionalized benzo[a]quinolizin-4-ones and pyrimido[6,1-a]isoquinoline derivatives [J].
Chakrabarti, S ;
Srivastava, MC ;
Ila, H ;
Junjappa, H .
SYNLETT, 2003, (15) :2369-2373