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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 3
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Original Articles

Simple and Efficient Method for Three-Component Synthesis of Spirooxindoles in Aqueous and Solvent-Free Media

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Pages 441-450 | Received 14 Sep 2009, Published online: 13 Jan 2011

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Read on this site (6)

Barkha K. Raheja & Dipak S. Dalal. (2023) Ammonium acetate mediated simple, rapid, and one-pot multicomponent synthesis of spirooxindole derivatives. Synthetic Communications 53:11, pages 808-822.
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Jannat Freidooni, Kurosh Rad-Moghadam & Maedeh Saeedi-Mirakmahaleh. (2022) ZrO2 and Rice-Husk-Xanthate Adduct: An Efficient Bioderived Catalyst for Synthesis of Spiro[4H-pyran-4,3′-indoline]s. Polycyclic Aromatic Compounds 42:10, pages 7217-7231.
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Majid Momahed Heravi, Tayebeh Momeni, Masoud Mirzaei, Vahideh Zadsirjan & Morteza Tahmasebi. (2021) An amino acid@isopolyoxometalate nanoparticles catalyst containing aspartic acid and octamolybdate for the synthesis of functionalized spirochromenes. Inorganic and Nano-Metal Chemistry 51:6, pages 896-909.
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Leila Moradi & Zeynab Ataei. (2017) Efficient and green pathway for one-pot synthesis of spirooxindoles in the presence of CuO nanoparticles. Green Chemistry Letters and Reviews 10:4, pages 380-386.
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Sayed Hossein Siadatifard, Masumeh Abdoli-Senejani & Mohammad Ali Bodaghifard. (2016) An efficient method for synthesis of bis(indolyl)methane and di-bis(indolyl)methane derivatives in environmentally benign conditions using TBAHS. Cogent Chemistry 2:1.
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Agus Rimus Liandi, Antonius Herry Cahyana, Diva Naufal Alfariza, Rahma Nuraini, Renita Wulan Sari & Tio Putra Wendari. (2024) Spirooxindoles: Recent report of green synthesis approach. Green Synthesis and Catalysis 5:1, pages 1-13.
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Pegah Mardaneh & Ali Reza Sardarian. (2023) Durable magnetite-chitosan core–shell nanoparticles as reusable green nanocatalyst for the benign one-pot three-component synthesis of spirooxindoles and spirochromenes at ambient temperature under both solvent-free and ultrasonic conditions in aqueous ethanol solution. Journal of the Iranian Chemical Society 21:1, pages 211-225.
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Wendy A. Loughlin & Asmaa Boufridi. 2022. Comprehensive Heterocyclic Chemistry IV. Comprehensive Heterocyclic Chemistry IV 638 725 .
Nipun Patel, Unnati Patel & Abhishek Dadhania. (2021) Highly efficient and green synthesis of spiro[indoline-3,9′-xanthene]trione and spiro[chromene-4,3′-indoline]-3-carbonitrile derivatives in water catalyzed by graphene oxide-supported dicationic ionic liquid. Research on Chemical Intermediates 47:6, pages 2189-2206.
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Fatemeh Kamali & Farhad Shirini. (2021) An efficient one-pot multi-component synthesis of spirooxindoles using Fe3O4/g-C3N4 nanocomposite as a green and reusable catalyst in aqueous media. Journal of Molecular Structure 1227, pages 129654.
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Bimal Krishna Banik, Bubun Banerjee, Gurpreet Kaur, Shivam Saroch & Rajat Kumar. (2020) Tetrabutylammonium Bromide (TBAB) Catalyzed Synthesis of Bioactive Heterocycles. Molecules 25:24, pages 5918.
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Ganesh A. Thakur, Rupashri K. KaduVishwanath R. Patil & Pramod B. Thakur. (2020) Progress in the Synthesis of Oxindole‐Naphthoquinone Molecular Hybrid Scaffolds: A Concise Review. ChemistrySelect 5:43, pages 13628-13643.
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Leila Youseftabar-Miri, Hamide Hosseinjani-Pirdehi, Ahmad Akrami & Sara Hallajian. (2020) Recent investigations in the synthesis of spirooxindole derivatives by Iranian researchers. Journal of the Iranian Chemical Society 17:9, pages 2179-2231.
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Shahrzad Abdolmohammadi, Seyed Reza Rasouli Nasrabadi, Mohammad Reza Dabiri & Sayed Mustafa Banihashemi Jozdani. (2020) TiO 2 Nanoparticles Immobilized on Carbon Nanotubes: An Efficient Heterogeneous Catalyst in Cyclocondensation Reaction of Isatins with Malononitrile and 4‐Hydroxycoumarin or 3,4‐Methylenedioxyphenol under Mild Reaction Conditions . Applied Organometallic Chemistry 34:4.
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Yogesh B. Wagh, Swapnil A. Padvi, Pramod P. Mahulikar & Dipak S. Dalal. (2019) CsF promoted rapid synthesis of spirooxindole‐pyran annulated heterocycles at room temperature in ethanol. Journal of Heterocyclic Chemistry 57:3, pages 1101-1110.
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Khadhar Navaz Umar Basha & Shanthi Gnanamani. (2019) An Efficient and Easy Method for the One‐pot Synthesis of Spirooxindoles in the Presence of Na 2 CO 3 . Journal of Heterocyclic Chemistry 56:7, pages 2008-2016.
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Naveen Gupta, Gopal Bhojani, Rajkumar Tak, Ajay Jakhar, Noor‐ul H. Khan, Shruti Chatterjee & Rukhsana I. Kureshy. (2017) Highly Diastereoselective Syntheses of Spiro‐Oxindole Dihydrofuran Derivatives in Aqueous Media and Their Antibacterial Activity. ChemistrySelect 2:33, pages 10902-10907.
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Alireza Hasaninejad, Fatemeh Mandegani, Maryam Beyrati, Ammar Maryamabadi & Gholamhossein Mohebbi. (2017) Highly Efficient Synthesis of Spirooxindole, Spiroacenaphthylene and Bisbenzo[b]pyran Derivatives and Evaluation of Their Inhibitory Activity against Sirtuin 2. ChemistrySelect 2:23, pages 6784-6796.
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Mo Zhang, Qiu-Yang Fu, Ge Gao, He-Ye He, Ying Zhang, Yin-Su Wu & Zhan-Hui Zhang. (2017) Catalyst-Free, Visible-Light Promoted One-Pot Synthesis of Spirooxindole-Pyran Derivatives in Aqueous Ethyl Lactate. ACS Sustainable Chemistry & Engineering 5:7, pages 6175-6182.
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Wafaa S. Hamama, Alaa El‐Din E. Hassanien & Hanafi H. Zoorob. (2017) Advanced Routes in Synthesis and Reactions of Lawsone Molecules (2‐Hydroxynaphthalene‐1,4‐dione). Journal of Heterocyclic Chemistry 54:4, pages 2155-2196.
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Shahrzad Javanshir, Nassim Saghiran Pourshiri, Zahra Dolatkhah & Mohammad Farhadnia. (2016) Caspian Isinglass, a versatile and sustainable biocatalyst for domino synthesis of spirooxindoles and spiroacenaphthylenes in water. Monatshefte für Chemie - Chemical Monthly 148:4, pages 703-710.
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Ahmad Reza Moosavi-ZareMohammad Ali ZolfigolRasoul Salehi-MoratabEhsan Noroozizadeh. (2017) Synthesis of spiropyran derivatives over 1-(carboxymethyl) pyridinium iodide as nanostructured pyridinium salt under aqueous media. Canadian Journal of Chemistry 95:2, pages 194-198.
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A. V. Andina & A. N. Andin. (2016) Recyclization of 5′-acetyl-2′-amino-6′-methyl-2-oxo-1,2-dihydrospiro[indole-3,4′-pyran]-3′-carbonitrile in reactions with some nitrogen binucleophiles. Russian Journal of Organic Chemistry 52:7, pages 1068-1069.
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Mosadegh Keshavarz. (2015) Ion-pair immobilization of l-prolinate anion onto cationic polymer support and a study of its catalytic activity for one-pot synthesis of spiroindolones. Journal of the Iranian Chemical Society 13:3, pages 553-561.
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Mohammad Ali Bodaghifard, Mohammad Solimannejad, Sajad Asadbegi & Samira Dolatabadifarahani. (2015) Mild and green synthesis of tetrahydrobenzopyran, pyranopyrimidinone and polyhydroquinoline derivatives and DFT study on product structures. Research on Chemical Intermediates 42:2, pages 1165-1179.
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Tetyana L. Pavlovska, Ruslan Gr. Redkin, Victoria V. Lipson & Dmytro V. Atamanuk. (2015) Molecular diversity of spirooxindoles. Synthesis and biological activity. Molecular Diversity 20:1, pages 299-344.
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Ghodsi Mohammadi Ziarani, Faezeh Aleali & Negar Lashgari. (2016) Recent applications of barbituric acid in multicomponent reactions. RSC Advances 6:56, pages 50895-50922.
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Mojtaba Baghernejad, Saeed Khodabakhshi & Sanaz Tajik. (2016) Isatin-based three-component synthesis of new spirooxindoles using magnetic nano-sized copper ferrite. New Journal of Chemistry 40:3, pages 2704-2709.
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Masoumeh Zakeri, Mohamed Mahmoud Nasef, Ebrahim Abouzari-Lotf, Arezoo Moharami & Majid M. Heravi. (2015) Sustainable alternative protocols for the multicomponent synthesis of spiro-4H-pyrans catalyzed by 4-dimethylaminopyridine. Journal of Industrial and Engineering Chemistry 29, pages 273-281.
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Abbas Rahmati & Neda Pashmforoush. (2014) Synthesis of various heterocyclic compounds via multi-component reactions in water. Journal of the Iranian Chemical Society 12:6, pages 993-1036.
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Hong‐Wu Zhao, Bo Li, Ting Tian, Wei Meng, Zhao Yang, Xiu‐Qing Song, Xiao‐Qin Chen & Hai‐Liang Pang. (2015) Highly Enantioselective Synthesis of Chiral Pyranonaphthoquinone‐Fused Spirooxindoles through Organocatalytic Three‐Component Cascade Reactions. European Journal of Organic Chemistry 2015:15, pages 3320-3326.
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Vijay V. Shinde, Mudumala Veeranarayana Reddy, Yong Hyun Kim, Byung Kwon Cho & Yeon Tae Jeong. (2014) Silica sodium carbonate: the most efficient catalyst for the one-pot synthesis of indeno[1,2-b]quinoline and spiro[chromene-4,3′-indoline]-3-carbonitriles under solvent-free condition. Monatshefte für Chemie - Chemical Monthly 146:4, pages 673-682.
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Mansoureh Daraie, Yahya S. Beheshtiha & Majid M. Heravi. (2014) Synthesis of spirochromene derivatives catalyzed by Mn(bpyo)2/MCM-41 in water. Monatshefte für Chemie - Chemical Monthly 146:1, pages 191-198.
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Negar Lashgari, Ghodsi Mohammadi Ziarani, Alireza Badiei & Mansoureh Zarezadeh‐Mehrizi. (2014) Application of Sulfonic Acid Functionalized SBA‐15 as a New Nanoporous Acid Catalyst in the Green One‐Pot Synthesis of Spirooxindole‐4 H ‐pyrans . Journal of Heterocyclic Chemistry 51:6, pages 1628-1633.
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Ghodsi Mohammadi Ziarani, Sakineh Faramarzi, Negar Lashgari & Alireza Badiei. (2013) A simple and clean method for multicomponent synthesis of spiro [indole-tetrahydropyrano(2,3-d)pyrimidine] derivatives using SBA-Pr-SO3H as catalyst under solvent-free conditions. Journal of the Iranian Chemical Society 11:3, pages 701-709.
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Ji Hyang Park, Yong Rok Lee & Sung Hong Kim. (2013) A novel synthesis of diverse 2-amino-5-hydroxy-4H-chromene derivatives with a spirooxindole nucleus by Ca(OH)2-mediated three-component reactions of substituted resorcinols with isatins and malononitrile. Tetrahedron 69:46, pages 9682-9689.
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Xiaoqing Liu, Xiaoling Xu, Xu Wang, Wenxin Yang, Qun Qian, Min Zhang, Liping Song, Hongmei Deng & Min Shao. (2013) A facile and convenient way to functionalized trifluoromethylated spirocyclic[indole-3,4-pyrano[2,3-c]pyrazole] derivatives. Tetrahedron Letters 54:33, pages 4451-4455.
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Guo‐Dong Wang, Xiao‐Nan Zhang & Zhan‐Hui Zhang. (2013) One‐Pot Three‐Component Synthesis of Spirooxindoles Catalyzed by Hexamethylenetetramine in Water. Journal of Heterocyclic Chemistry 50:1, pages 61-65.
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Ghodsi MOHAMMADI ZIARANI, Alireza BADIEI, Somayeh MOUSAVI, Negar LASHGARI & Afsaneh SHAHBAZI. (2012) Application of Amino-Functionalized SBA-15 Type Mesoporous Silica in One-Pot Synthesis of Spirooxindoles. Chinese Journal of Catalysis 33:11-12, pages 1832-1839.
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Igor V. Magedov, Artem S. Kireev, Aaron R. Jenkins, Nikolai M. Evdokimov, Dustin T. Lima, Paul Tongwa, Jeff Altig, Wim F. A. Steelant, Severine Van slambrouck, Mikhail Yu. Antipin & Alexander Kornienko. (2012) Structural simplification of bioactive natural products with multicomponent synthesis. 4. 4H-Pyrano-[2,3-b]naphthoquinones with anticancer activity. Bioorganic & Medicinal Chemistry Letters 22:16, pages 5195-5198.
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Maya Shankar Singh & Sushobhan Chowdhury. (2012) Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis. RSC Advances 2:11, pages 4547.
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Yanlong Gu. (2012) Multicomponent reactions in unconventional solvents: state of the art. Green Chemistry 14:8, pages 2091.
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Akbar Mobinikhaledi, Naser Foroughifar & Mohammad Ali Bodaghi Fard. (2011) ChemInform Abstract: Simple and Efficient Method for Three‐Component Synthesis of Spirooxindoles in Aqueous and Solvent‐Free Media.. ChemInform 42:30.
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