Stereoselective synthesis of oxazolidine, hexahydropyrrolo [2,1-b] oxazole, and tetrahydro-2H-oxazolo [3,2-c] thiazole grafted macrocycles through intramolecular 1,3-dipolar cycloaddition reaction

被引:26
作者
Purushothaman, S. [1 ]
Raghunathan, R. [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
Macrocycles; 1,3-DC reaction; Stereoselective; Oxazolidine; Pyrrolo oxazlole; Oxazolothiazole; AZOMETHINE YLIDES; CONVENIENT-SYNTHESIS; CYCLOPHANE; RECOGNITION; 1-OXAPYRROLIZIDINES; FACILE; RINGS;
D O I
10.1016/j.tetlet.2009.09.122
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile one-pot synthesis of oxazolidine, hexahydropyrrolooxazole and tetrahydro-2H-oxazolothiazole grafted macrocycles through intramolecular 1,3-dipolar cycloaddition reaction (1,3-DC reaction) is reported. X-ray diffraction studies and 2D NOESY experiments of the cycloadducts proved the stereo- and regiochemistry of the cycloaddition. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6848 / 6850
页数:3
相关论文
共 32 条
[1]   Stereoselective synthesis of bis-β-lactam grafted macrocycles [J].
Arumugam, Natarajan ;
Raghunathan, Raghavachary .
TETRAHEDRON LETTERS, 2006, 47 (50) :8855-8857
[2]   An easy access to novel steroidal dispiropyrrolidines through 1,3-dipolar cycloaddition of azomethine ylides [J].
Babu, A. R. Suresh ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2008, 49 (31) :4618-4620
[3]   Synthesis of ferrocenyl monospirooxindolopyrrolidines-a facile [3+2]-cycloaddition of azomethine ylides [J].
Babu, A. R. Suresh ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2008, 49 (29-30) :4487-4490
[4]   Incorporation of group 14 elements into siloxane-bridged paracyclophanes cyclo-[p,p′-Me2SiC6H4EMe2C6H4SiMe2O]2 (E = C, Si, Ge, Sn) [J].
Beckmann, J ;
Duthie, A ;
Reeske, G ;
Schürmann, M .
ORGANOMETALLICS, 2005, 24 (15) :3629-3633
[5]   Calculated chemical shifts as a fine tool of conformational analysis: An unambiguous solution for haouamine alkaloids [J].
Belostotskii, Anatoly M. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15) :5723-5731
[6]   A novel strained undecadiyne cyclophane with interesting dienophilic character [J].
Collins, SK ;
Yap, GPA ;
Fallis, AG .
ORGANIC LETTERS, 2002, 4 (01) :11-14
[7]   Synthesis and solid-state structures of new cyclophane host molecules [J].
Czech, Bronislaw P. ;
Kus, Piotr ;
Stetson, Christopher M. ;
Dalley, N. Kent ;
Bartsch, Richard A. .
TETRAHEDRON, 2007, 63 (06) :1360-1365
[8]  
DURGA RR, 2006, TETRAHEDRON, V62, P12357
[9]   INTRAMOLECULAR CYCLOADDITIONS WITH AZOMETHINE YLIDES FOR THE SYNTHESIS OF METACYCLOPHANES [J].
EBERBACH, W ;
FRITZ, H ;
HEINZE, I ;
VONLAER, P ;
LINK, P .
TETRAHEDRON LETTERS, 1986, 27 (34) :4003-4006
[10]  
FORTE M, 1985, GAZZ CHIM ITAL, V115, P569