Abstract:
The zwitterionic 1:1 intermediates formed in the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates are trapped by 2,4-thiazolidine-2,4-diones to afford N-functionalized 2,4-dioxothiazolidines containing a ketenimine moiety.
Citation:
I. Yavari, T. Sanaeishoar, L. Azad, M. Ghazvini, “Ketenimine N-functionalization of thiazolidine-2,4-diones with acetylenes and isocyanides”, Mendeleev Commun., 21:2 (2011), 108–109
Linking options:
https://www.mathnet.ru/eng/mendc2883
https://www.mathnet.ru/eng/mendc/v21/i2/p108
This publication is cited in the following 13 articles:
Issa Yavari, Somayeh Akbarzadeh, Meysam Ghorbanzadeh, “Formation of quinazolin-4(3H)-ones from N-sulfonoketenimines and 2-aminobenzamides”, J IRAN CHEM SOC, 21:4 (2024), 1011
Leili Shaker Ardakani, Mohammad H. Mosslemin, Alireza Hassanabadi, Saeedeh Hashemian, “Reaction between Benzoic Acid N′-(2-Oxo-2-Phenyl-Ethyl)Hydrazide and Acetylenic Esters in the Presence of Alkyl Isocyanides: One-Pot Synthesis of Highly Functionalized 2,3-Dihydro-1H-Pyrazoles”, Polycyclic Aromatic Compounds, 42:10 (2022), 6861
Issa Yavari, Meysam Ghorbanzadeh, Somayeh Akbarzadeh, “A synthesis of fuctionalized 2-amino-3-cyano pyrroles from terminal alkynes, sulfonyl azides and phenacylmalononitriles”, Org. Biomol. Chem., 20:21 (2022), 4352
Rosa Edris Ameri, Bita Mohtat, Eskandar Alipour, Behrooz Mirza, “An Isocyanide Based Three-component Reaction under Catalyst-free Conditions for Synthesis of New and Stable Trifluoromethylated Ketenimines and 1-Azabutadienes”, Organic Preparations and Procedures International, 52:1 (2020), 37
Leila Azad, Maryam Ghazvini, Haleh Sanaeishoar, Issa Yavari, “Synthesis of functionalized 1,2-dihydroisoquinolines via one-pot reactions of isoquinoline, alkyl propiolate, and thiazolidin-2,4-dione”, Journal of Chemical Research, 43:11-12 (2019), 457
Samahe Sadjadi, Majid M. Heravi, Niousha Nazari, “Isocyanide-based multicomponent reactions in the synthesis of heterocycles”, RSC Adv., 6:58 (2016), 53203
Sadegh Rostamnia, “In situ generation and protonation of the isocyanide/acetylene adduct: a powerful catalyst-free strategy for multicomponent synthesis of ketenimines, aza-dienes, and heterocycles”, RSC Adv., 5:117 (2015), 97044
Sadegh Rostamnia, Esmail Doustkhah, Green Chemistry: Synthesis of Bioactive Heterocycles, 2014, 253
Hamideh Emtiazi, Mohammad A. Amrollahi, “Catalyst‐Free One‐Pot Synthesis of Ketene Imines under Ultrasound Irradiation”, Helvetica Chimica Acta, 97:10 (2014), 1422
Ali Souldozi, Amir Hossein Pourasad Balderlo, “Multicomponent Reactions of Isocyanides and Dialkyl Acetylenedicarboxylate in the Presence of 2-Hydroxy-3-Methyl-2-Cyclopentene-1-One: One-Pot Synthesis of 1-Azadienes in Water”, Journal of Chemical Research, 38:1 (2014), 62
Tayebeh Sanaeishoar, Fouad Mohave, “Three-Component coupling of Alkyl/Aryl Isocyanides, Acetylene Dicarboxylates and (2,4-Dioxothiazolidin-3-Yl)Acetic Acids”, Journal of Chemical Research, 38:8 (2014), 470
Ping Lu, Yanguang Wang, “The thriving chemistry of ketenimines”, Chem. Soc. Rev., 41:17 (2012), 5687
Issa Yavari, Tayebeh Sanaeishoar, Leila Azad, Maryam Ghazvini, “ChemInform Abstract: Ketenimine N‐Functionalization of Thiazolidine‐3,4‐diones with Acetylenes and Isocyanides.”, ChemInform, 42:34 (2011)
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