Draft Pyridazinones from Maleic Hydrazide: A New Substrate for the Mitsunobu Reaction Journal: Canadian Journal of Chemistry Manuscript ID cjc-2019-0474.R1 Manuscript Type: Article Date Submitted by the Author: 15-Jan-2020 Complete List of Authors: Rodriguez, Christina; Wilfrid Laurier University, Department of Chemistry and Biochemistry Kiriakopoulos, Rachel; Wilfrid Laurier University, Department of Chemistry and Biochemistry Hiscock, Lana; Wilfrid Laurier University, Department of Chemistry and Biochemistry Schroeder, Zachary; Wilfrid Laurier University, Department of Chemistry and Biochemistry Dawe, Louise; Wilfrid Laurier University, Department of Chemistry and Biochemistry Is the invited manuscript for consideration in a Special Issue?: J Wuest Keyword: Crystal engineering, Mitsunobu reaction, pyridazinones, pyridazinols, Cambridge Structural Database analysis https://mc06.manuscriptcentral.com/cjc-pubs Canadian Journal of Chemistry
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Draft
Pyridazinones from Maleic Hydrazide: A New Substrate for the Mitsunobu Reaction
Journal: Canadian Journal of Chemistry
Manuscript ID cjc-2019-0474.R1
Manuscript Type: Article
Date Submitted by the Author: 15-Jan-2020
Complete List of Authors: Rodriguez, Christina; Wilfrid Laurier University, Department of Chemistry and BiochemistryKiriakopoulos, Rachel; Wilfrid Laurier University, Department of Chemistry and BiochemistryHiscock, Lana; Wilfrid Laurier University, Department of Chemistry and BiochemistrySchroeder, Zachary; Wilfrid Laurier University, Department of Chemistry and BiochemistryDawe, Louise; Wilfrid Laurier University, Department of Chemistry and Biochemistry
Is the invited manuscript for consideration in a Special
Examination of extended packing for 4 (Figure 5) suggested that there may be -stacking of the
terminal pyridyl rings parallel to the crystallographic b-axis, however, ring centroid-to-centroid
distances (4.06086(15) Å to 2−x, -1−y, −z and 4.24490(16) Å to 2−x, −y, −z) exceed what is
considered to be any meaningful interaction.
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Figure 5. Extended packing diagram for 4. Pyridyl rings represented as 50% displacement
ellipsoids, and all other atoms represented as capped sticks. Hydrogen atoms omitted for clarity.
Attempts to coordinate 2, 3, and 4 with first row transition metal cations were undertaken using a
variety of methods, including direct combination of ligand and metal salts in heated solvents
(including methanol, ethanol, acetonitrile and toluene) and with the addition of base
(trimethylamine or aqueous sodium/potassium hydroxide), ball milling and microwave reactions.
Despite many efforts, little evidence of coordination was observed (i.e. colour changes or
precipitation upon reaction), and we suspect that this difficulty was in part due to poor ligand
solubility. Colour changes were observed upon reaction of 2 with Cu(ClO4)2, and 4 with CoCl2
or Co(NO3)2, and subsequently, X-ray quality crystals were obtained. Disappointingly, in each
case, these were previously reported (Cu(CH3CN)4(ClO4),20 [CoCl4][Co(DMSO)6]221), or new
solvates ([Co(DMSO)6](NO3)2.2H2O)22 of known metal salts, and no organic ligands were
present.
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Conclusions
We have shown that maleic hydrazide is a suitable substrate for the Mitsunobu reaction, and that
the product of this process is an asymmetric pyridazinone. Our initial goal was to construct
flexible porous architectures by a combination of strong hydrogen bonding dimers and metal-to-
ligand coordination chemistry. We demonstrated that the hydrogen bonding dimer is conserved
in the case of 4, however, construction of porous architectures has so far eluded us. This design
strategy can now be considered for introduction of stronger Lewis base functionality towards our
original goal.
Notes
CCDC 1966083 contain the supplementary crystallographic data for this paper. These data can
be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing
[email protected], or by contacting The Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
Acknowledgment
LND is grateful to the Natural Sciences and Engineering Research Council of Canada (NSERC),
the Canada Foundation for Innovation, and Wilfrid Laurier University for financial support. This
work was also supported by the Research Support Fund. LKH acknowledges an NSERC
Postgraduate Award (PGS-M) and an Ontario Graduate Scholarship for support. Delara Joekar,
Wilfrid Laurier University, is acknowledged for assistance with collection of IR spectra and
melting point data. Dr. Paul D. Boyle, Department of Chemistry X-Ray Facility, Western
University, London, ON, Canada, is acknowledged for assistance with X-ray data collection.
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