Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles

被引:30
作者
Arumugam, Natarajan [1 ]
Kumar, Raju Suresh [1 ]
Almansour, Abdulrahman I. [1 ]
Perumal, Subbu [2 ]
机构
[1] King Saud Univ, Coll Sci, Dept Chem, Riyadh 11451, Saudi Arabia
[2] Madurai Kamaraj Univ, Sch Chem, Dept Organ Chem, Madurai 625021, Tamil Nadu, India
关键词
Multicomponent; 1,3-Dipolar cycloadditions; Spiroheterocycles; Azomethine ylides and Nitrile oxides; AZOMETHINE YLIDE CYCLOADDITION; BAYLIS-HILLMAN ADDUCTS; STEREOSELECTIVE-SYNTHESIS; REGIOSELECTIVE-SYNTHESIS; ONE-POT; FACILE SYNTHESIS; DISPIRO HETEROCYCLES; BETA-LACTAMS; IONIC LIQUID; PYRROLIDINES;
D O I
10.2174/13852728113179990091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spiroheterocyclic ring systems are attractive synthetic targets due to their interesting conformational features and their structural implications on their activity in biological systems. Consequently, a vast deal of research by synthetic organic as well as medicinal chemists pertains to the synthesis of these heterocycles employing diverse synthetic methodologies. Among them, one-pot multicomponent 1,3-cycloaddition reactions have emerged as preferred synthetic protocol in view of their convergence, atom economy, eco-friendliness, flexibility and facile automation. This review article focuses on the assembly of mono-, di- and multispiro heterocyclic hybrids via aforesaid synthetic methodologies with a variety of dipolarophiles.
引用
收藏
页码:1929 / 1956
页数:28
相关论文
共 76 条
[1]   AChE inhibitor: A regio- and stereo-selective 1,3-dipolar cycloaddition for the synthesis of novel substituted 5,6-dimethoxy spiro[5.3′]-oxindole-spiro-[6.3"]-2,3-dihydro-1H-inden-1"-one-7-(substituted aryl)-tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole [J].
Ali, Mohamed Ashraf ;
Ismail, Rusli ;
Choon, Tan Soo ;
Kumar, Raju Suresh ;
Osman, Hasnah ;
Arumugam, Natarajan ;
Almansour, Abdulrahman I. ;
Elumalai, Karthikeyan ;
Singh, Abhimanyu .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (01) :508-511
[2]   An experimental and theoretical investigation of the regio- and stereoselectivity of the polar [3+2] cycloaddition of azomethine ylides to nitrostyrenes [J].
Alimohammadi, Kamal ;
Sarrafi, Yaghoub ;
Tajbakhsh, Mahmood ;
Yeganegi, Saeed ;
Hamzehloueian, Mahshid .
TETRAHEDRON, 2011, 67 (08) :1589-1597
[3]   A novel access to highly functionalised β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction [J].
Arumugam, N ;
Jayashankaran, J ;
Manian, RDRS ;
Raghunathan, R .
TETRAHEDRON, 2005, 61 (35) :8512-8516
[4]   Synthesis and antimicrobial activity of highly functionalised novel β-lactam grafted spiropyrrolidines and pyrrolizidines [J].
Arumugam, Natarajan ;
Periyasami, Govindasami ;
Raghunathan, Raghavachary ;
Kamalraj, Subban ;
Muthumary, Johnpaul .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (02) :600-607
[5]   FACILE SYNTHESIS OF β-LACTAM-GRAFTED SPIROOXINDOLOPYRROLIDINE THROUGH REGIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION REACTION [J].
Arumugam, Natarajan ;
Raghunathan, Raghavachary .
SYNTHETIC COMMUNICATIONS, 2011, 41 (18) :2747-2755
[6]   Catalytic asymmetric synthesis of quaternary carbon centers.: Exploratory investigations of intramolecular Heck reactions of (E)-α,β-Unsaturated 2-haloanilides and analogues to form enantioenriched spirocyclic products [J].
Ashimori, A ;
Bachand, B ;
Overman, LE ;
Poon, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (26) :6477-6487
[7]   A facile entry into a novel class of dispiroheterocyclic framework through 1,3-dipolarcycloaddition of azomethine ylides with 3-arylidene-4-chromanones as dipolarophiles [J].
Augustine, T. ;
Kanakam, Charles C. ;
Vithiya, Scholastica Mary ;
Ramkumar, V. .
TETRAHEDRON LETTERS, 2009, 50 (43) :5906-5909
[8]   Heteropolyacid-silica mediated [3+2] cycloaddition of azomethine ylides - a facile multicomponent one-pot synthesis of novel dispiroheterocycles [J].
Babu, A. R. Suresh ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2006, 47 (52) :9221-9225
[9]   A facile synthesis of novel ferrocene grafted spiro-indenoquinoxaline pyrrolizidines via one-pot multicomponent [3+2] cycloaddition of azomethine ylides [J].
Babu, A. R. Suresh ;
Gavaskar, D. ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2012, 53 (49) :6676-6681
[10]   An expedient synthesis of ferrocene grafted spirooxindolopyrrolizidines via [3+2]-cycloaddition of azomethine ylides [J].
Babu, A. R. Suresh ;
Raghunathan, R. ;
Baskaran, Sundari .
TETRAHEDRON, 2009, 65 (11) :2239-2243