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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 36, 2006 - Issue 2
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Original Articles

Regioselective Synthesis of Novel Spirooxindolo and Spiroindano Nitro Pyrrolidines Through 3+2 Cycloaddition Reaction

Mahalingam Poornachandran Department of Organic Chemistry, University of Madras, Guindy, Chennai, India
,
Rajendran Muruganantham Department of Organic Chemistry, University of Madras, Guindy, Chennai, India
&
Ragavachary Raghunathan Department of Organic Chemistry, University of Madras, Guindy, Chennai, IndiaCorrespondence[email protected]
Pages 141-150 | Received 15 Jul 2005, Published online: 15 Aug 2006

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MayuriA. Borad, ManojN. Bhoi, NeelamP. Prajapati & HiteshD. Patel. (2014) Review of Synthesis of Spiro Heterocyclic Compounds from Isatin. Synthetic Communications 44:7, pages 897-922.
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Reza Heydari, Batool Tahamipour, Niloofar Akbarzadeh Torbati, Claudia Graiff & Morteza Ziyaadini. (2013) One-Pot Synthesis and X-Ray Structure of New, Stable Tetrahydropyrrolo [1,2-a][1,10]phenanthrolines with Four Diastereoisomeric Centers. Synthetic Communications 43:15, pages 2031-2041.
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Mahalingam Poornachandran, Mathesan Jayagobi & Raghavachary Raghunathan. (2010) Regioselective Synthesis of Dispirocycloalkanooxindolopyrrolidines and Dispirocyclalkanoindanopyrrolidines. Synthetic Communications 40:4, pages 551-563.
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Mahalingam Poornachandran & Ragavachary Raghunathan. (2007) Synthesis of Spirooxindolo/Spiroindano Nitro Pyrrolizidines through Regioselective Azomethine Ylide Cycloaddition Reaction. Synthetic Communications 37:15, pages 2507-2517.
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Articles from other publishers (25)

Madhuri P Rao, Anu Chauhan, Lucia Pintilie, Sudheer Kumar Singh & Madhu Ganesh. (2023) Concise route to stereoselective chlorobenzene-based spiropyrrolidine oxindoles for pursuit as antitubercular agents. Journal of Chemical Sciences 135:2.
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I. Z. Musabirov & R. R. Gataullin. (2022) New Synthetic Approaches to Benzo-Fused Spiro Heterocycles. Russian Journal of Organic Chemistry 58:10, pages 1369-1397.
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Nilamuni H. de Silva, Suneela Pyreddy, Ewan W. Blanch, Helmut M. Hügel & Subashani Maniam. (2021) Microwave-assisted rapid synthesis of spirooxindole-pyrrolizidine analogues and their activity as anti-amyloidogenic agents. Bioorganic Chemistry 114, pages 105128.
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Igor B. Kutyashev, Maria V. Ulitko, Alexey Yu. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev & Vyacheslav Ya. Sosnovskikh. (2019) A regio- and stereocontrolled approach to the synthesis of 4-CF 3 -substituted spiro[chromeno[3,4- c ]pyrrolidine-oxindoles] via reversible [3+2] cycloaddition of azomethine ylides generated from isatins and sarcosine to 3-nitro-2-(trifluoromethyl)-2 H -chromenes . New Journal of Chemistry 43:47, pages 18495-18504.
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Madhuri P. Rao, Shubha S. Gunaga, Johannes Zuegg, Rambabu Pamarthi & Madhu Ganesh. (2019) Highly regio- and diastereoselective [3 + 2]-cycloadditions involving indolediones and α,β-disubstituted nitroethylenes. Organic & Biomolecular Chemistry 17:42, pages 9390-9402.
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Ying Huang, Yi-Xin Huang, Jing Sun & Chao-Guo Yan. (2018) Diastereoselective synthesis of dispirooxindoles via [3+2] cycloaddition of azomethine ylides to 3-phenacylideneoxindoles and evaluation of their cytotoxicity . RSC Advances 8:42, pages 23990-23995.
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Ying Huang, Wei Min, Qiu-Wen Wu, Jing Sun, Da-Hua Shi & Chao-Guo Yan. (2018) Facile one-pot synthesis of spirooxindole-pyrrolidine derivatives and their antimicrobial and acetylcholinesterase inhibitory activities. New Journal of Chemistry 42:19, pages 16211-16216.
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Aleksey Yi. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev, Igor B. Kutyashev, Vladimir S. Moshkin & Vyacheslav Ya. Sosnovskikh. (2017) Regio- and stereoselective 1,3-dipolar cycloaddition of indenoquinoxalinone azomethine ylides to β-nitrostyrenes: synthesis of spiro[indeno[1,2-b]quinoxaline-11,3'-pyrrolizidines] and spiro[indeno[1,2-b]quinoxaline-11,2'-pyrrolidines]. Chemistry of Heterocyclic Compounds 53:4, pages 451-459.
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Andreas Gollner, Dorothea Rudolph, Heribert Arnhof, Markus Bauer, Sophia M. Blake, Guido Boehmelt, Xiao-Ling Cockroft, Georg Dahmann, Peter Ettmayer, Thomas Gerstberger, Jale Karolyi-Oezguer, Dirk Kessler, Christiane Kofink, Juergen Ramharter, Jörg Rinnenthal, Alexander Savchenko, Renate Schnitzer, Harald Weinstabl, Ulrike Weyer-Czernilofsky, Tobias Wunberg & Darryl B. McConnell. (2016) Discovery of Novel Spiro[3 H -indole-3,2′-pyrrolidin]-2(1 H )-one Compounds as Chemically Stable and Orally Active Inhibitors of the MDM2–p53 Interaction . Journal of Medicinal Chemistry 59:22, pages 10147-10162.
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Alexey Yu. Barkov, Nikolay S. Zimnitskiy, Vladislav Yu. Korotaev, Igor B. Kutyashev, Vladimir S. Moshkin & Vyacheslav Ya. Sosnovskikh. (2016) Highly regio- and stereoselective 1,3-dipolar cycloaddition of stabilised azomethine ylides to 3,3,3-trihalogeno-1-nitropropenes: synthesis of trihalomethylated spiro[indoline-3,2′-pyrrolidin]-2-ones and spiro[indoline-3,3′-pyrrolizin]-2-ones. Tetrahedron 72:43, pages 6825-6836.
Crossref
Robert R. P. Torregrosa. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis 1 4 .
Biswajit Gayen & Avijit Banerji. (2014) Simple and efficient routes to substituted oxazolidine and spiro-oxindole systems by one-pot synthetic strategies. Monatshefte für Chemie - Chemical Monthly 145:12, pages 1953-1965.
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Wahid Bux Jatoi, Philippe Puget, Ashique Hussain Jatoi & Ghulam Qadir Shar. (2014) Synthesis of Spirooxindoles: Compounds of Wide Therapeutical Applications. Pharmaceutical Chemistry Journal 48:4, pages 288-291.
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Min Xia & Ru-Zheng Ma. (2014) Recent Progress on Routes to Spirooxindole Systems Derived from Isatin. Journal of Heterocyclic Chemistry 51:3, pages 539-554.
Crossref
Kamal Alimohammadi, Yaghoub Sarrafi & Bahareh Rajabpour. (2014) An expedient approach for the regio- and stereoselective synthesis of novel spiroindolizidines via [3+2] cycloaddition. Comptes Rendus Chimie 17:2, pages 156-163.
Crossref
Abdolali Alizadeh & Javad Mokhtari. (2011) Novel four-component route to the synthesis of spiro[indoline-3,4′-pyridine]-3′-carboxylate derivatives. Tetrahedron 67:19, pages 3519-3523.
Crossref
Stephen Michael Rajesh, Subbu Perumal, J. Carlos Menéndez, Perumal Yogeeswari & Dharmarajan Sriram. (2011) Antimycobacterial activity of spirooxindolo-pyrrolidine, pyrrolizine and pyrrolothiazole hybrids obtained by a three-component regio- and stereoselective 1,3-dipolar cycloaddition. MedChemComm 2:7, pages 626.
Crossref
Hui Chen & Daqing Shi. (2010) Efficient One-Pot Synthesis of Novel Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium. Journal of Combinatorial Chemistry 12:4, pages 571-576.
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Mahalingam Poornachandran, Mathesan Jayagobi & Raghavachary Raghunathan. (2009) Regioselective Synthesis of rac -(1R,4R,6 R ,6a R )-6′-phenyl-7′,8′-dihydro-1″ H ,2′ H ,6′ H -dispiro[cycloalkane-1,5′-pyrrolo[1,2- c ][1,3]thiazole-4′,3″-indole]-2,2″-diones through 3 + 2 cycloaddition Reaction . Journal of Chemical Research 2009:4, pages 240-243.
Crossref
Ronald Grigg, Colin Kilner, Mohammed A.B. Sarker, Cecilia Orgaz de la Cierva & H. Ali Dondas. (2008) X=Y–ZH compounds as potential 1,3-dipoles. Part 64: Synthesis of highly substituted conformationally restricted and spiro nitropyrrolidines via Ag(I) catalysed azomethine ylide cycloadditions. Tetrahedron 64:37, pages 8974-8991.
Crossref
Mahalingam Poornachandran & Raghavachary Raghunathan. (2008) Synthesis of pyrrolo[3,4-b]pyrroles and perhydrothiazolo[3′,4′-2,3]pyrrolo[4,5-c]pyrroles. Tetrahedron 64:27, pages 6461-6474.
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Sarah R. Yong, Alison T. Ung, Stephen G. Pyne, Brian W. Skelton & Allan H. White. (2007) Syntheses of spiro[cyclopropane-1,3′-oxindole]-2-carboxylic acid and cyclopropa[c]quinoline-7b-carboxylic acid and their derivatives. Tetrahedron 63:5, pages 1191-1199.
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Mahalingam Poornachandran & Ragavachary Raghunathan. (2006) Synthesis of dispirooxindolecycloalka[d]pyrimidino[2,3-b]-thiazole pyrrolidine/thiapyrrolizidine ring systems. Tetrahedron 62:48, pages 11274-11281.
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Ronald Grigg & Mohammed Abul Basher Sarker. (2006) XY–ZH compounds as potential 1,3-dipoles. Part 63: Silver catalysed azomethine ylide cycloaddition—the synthesis of spiro homoserine lactone analogues. Tetrahedron 62:44, pages 10332-10343.
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Mahalingam Poornachandran, Rajendran Muruganantham & Ragavachary Raghunathan. (2006) Regioselective Synthesis of Novel Spirooxindolo and Spiroindano Nitro Pyrrolidines Through [3 + 2] Cycloaddition Reaction.. ChemInform 37:22.
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