Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines

Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines Publisher Pubmed

Haghipour S¹ ; Mehrdad M¹ ; Hosseini S³ ; Moazzam A² ; Radmoghadam K¹ ; Mahdavi M²

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1. Department of Chemistry, Faculty of Science, University of Guilan, Rasht, Iran
2. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
3. Shahid Beheshti University of Medical Sciences, Tehran, Iran

Source: Molecular Diversity Published:2023

Abstract

This paper describes the development of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate compound as a heterocyclic enols containing a Michael acceptor so that it participates in an Ugi-type multicomponent condensation through a Smiles rearrangement in replacement of acid components. The new four-component containing 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate, aldehyde derivatives, amine derivatives and isocyanides process leads readily and efficiently to heterocyclic enamines. This report is an outstanding strategy for the preparation of new biologically structures containing peptidic or pseudo-peptidic with quinolin-2(1H)-one scaffolds. Graphical abstract: [Figure not available: see fulltext.] © 2023, The Author(s), under exclusive licence to Springer Nature Switzerland AG.

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Experts (# of related papers)

Bagher Larijani (2)

Mohammad Mahdavi (2)

Style	Citing Format
MLA	Haghipour S, et al.. "Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines." Molecular Diversity, vol. 27, no. 5, 2023, pp. 2345-2352.
APA	Haghipour S, Mehrdad M, Hosseini S, Moazzam A, Radmoghadam K, Mahdavi M (2023). Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines. Molecular Diversity, 27(5), 2345-2352.
Chicago	Haghipour S, Mehrdad M, Hosseini S, Moazzam A, Radmoghadam K, Mahdavi M. "Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines." Molecular Diversity 27, no. 5 (2023): 2345-2352.
Harvard	Haghipour S et al. (2023) 'Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines', Molecular Diversity, 27(5), pp. 2345-2352.
Vancouver	Haghipour S, Mehrdad M, Hosseini S, Moazzam A, Radmoghadam K, Mahdavi M. Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines. Molecular Diversity. 2023;27(5):2345-2352.
BibTex	@article{ author = {Haghipour S and Mehrdad M and Hosseini S and Moazzam A and Radmoghadam K and Mahdavi M}, title = {Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines}, journal = {Molecular Diversity}, volume = {27}, number = {5}, pages = {2345-2352}, year = {2023} }
RIS	TY - JOUR AU - Haghipour S AU - Mehrdad M AU - Hosseini S AU - Moazzam A AU - Radmoghadam K AU - Mahdavi M TI - Ethyl 4-Hydroxy-2-Oxo-1,2-Dihydroquinoline-3-Carboxylate in the Smiles Rearrangement Reaction: Straightforward Synthesis of Amino Acid Derived Quinolin-2(1H)-One Enamines JO - Molecular Diversity VL - 27 IS - 5 SP - 2345 EP - 2352 PY - 2023 ER -

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