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Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones

Saiz, C and Pizzo, C and Manta, E and Wipf, P and Mahler, SG (2009) Microwave-assisted tandem reactions for the synthesis of 2-hydrazolyl-4-thiazolidinones. Tetrahedron Letters, 50 (8). 901 - 904. ISSN 0040-4039

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A tandem method for the synthesis of 2-hydrazolyl-4-thiazolidinones (5) from commercially available materials in a 3-component reaction has been developed. The reaction connects aldehydes, thiosemicarbazides, and maleic anhydride, effectively assisted by microwave irradiation. The synthesis of a new type of compound, 2-hydrazolyl-5,5-diphenyl-4-thiazolidinone (7), obtained by treatment of thiosemicarbazone with benzil in basic media is also reported. HOMO/LUMO energies, orbital coefficients, and charge distribution were used to explain the proposed reaction mechanism. © 2008 Elsevier Ltd.


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Item Type: Article
Status: Published
CreatorsEmailPitt UsernameORCID
Saiz, C
Pizzo, C
Manta, E
Wipf, Ppwipf@pitt.eduPWIPF
Mahler, SG
Date: 25 February 2009
Date Type: Publication
Journal or Publication Title: Tetrahedron Letters
Volume: 50
Number: 8
Page Range: 901 - 904
DOI or Unique Handle: 10.1016/j.tetlet.2008.12.020
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4039
PubMed Central ID: PMC2743427
PubMed ID: 19756224
Date Deposited: 03 Jul 2013 14:50
Last Modified: 02 Feb 2019 15:57


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