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Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple precursors : synthesis, spectroscopic characterization and the structures of an intermediate and two products

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Date
10/2021
Author
Mahesha, Ninganayaka
Yathirajan, Hemmige S.
Banu, Holalagudu A. Nagma
Kalluraya, Balakrishna
Rathore, Ravindranath S.
Glidewell, Christopher
Keywords
Crystal structure
Heterocyclic compounds
Hydrogen bonding
Molecular structure
NMR spectroscopy
Pyrazoles
Supramolecular assembly
Synthesis
Thiazoles
QD Chemistry
DAS
NIS
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Abstract
Two new 1-(thiazol-2-yl)-4,5-dihydropyrazoles have been synthesized from simple precursors, and characterized both spectroscopically and structurally. In addition, two intermediates in the reaction pathway have been isolated and characterized, one of them structurally. The molecules of the intermediate (E)-1-(4-methoxyphenyl)-3-[4-(prop-2-ynyloxy)phenyl]prop-2-en-1-one, C19H16O3 (I), are linked by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds to form ribbons. The products (RS)-5-(4-methoxyphenyl)-1-(4-phenythiazol-2-yl)-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1H-pyrazole, C28H23N3O2S (II), and (RS)-5-(4-methoxyphenyl)-1-[4-(4-methylphenyl)thiazol-2-yl]-3-[4-(prop-2-ynyloxy)phenyl]-4,5-dihydro-1H-pyrazole, C29H25N3O2S (III), are closely related-differing only by presence or absence of a methyl group at the arylthiazolyl substituent-and crystallize in an isomorphous setting. Both molecules contain an effectively planar dihydro-pyrazole ring, and possess an overall T-shaped structure, which is a characteristic of triaryl-substituted 4,5-dihydro-1-(thiazol-2-yl)pyrazole compounds. The crystal packing is characterized by intermolecular C-H⋯S and C-H⋯π (aryl/alkyne) interactions. A combination of two C-H⋯π(arene) hydrogen bonds links the product molecules into sheets.
Citation
Mahesha , N , Yathirajan , H S , Banu , H A N , Kalluraya , B , Rathore , R S & Glidewell , C 2021 , ' Formation of 1-(thiazol-2-yl)-4,5-dihydropyrazoles from simple precursors : synthesis, spectroscopic characterization and the structures of an intermediate and two products ' , Acta Crystallographica Section E: Crystallographic Communications , vol. 77 , no. Part 10 , pp. 975-981 . https://doi.org/10.1107/S2056989021009312
Publication
Acta Crystallographica Section E: Crystallographic Communications
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2056989021009312
ISSN
2056-9890
Type
Journal article
Rights
Copyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Description
HSY is grateful to the UGC, New Delhi, for the award of a BSR Faculty Fellowship for three years.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/24274

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