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New C‐3 Substituted 1 H ‐ and 2 H ‐Indazolephosphonic Acid Regioisomers: Synthesis, Spectroscopic Characterization and X‐Ray Diffraction Studies
Author(s) -
Teixeira Fátima C.,
Antunes Inês F.,
Curto M. João M.,
Duarte M. Teresa,
André Vânia,
Teixeira António P. S.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202102538
Subject(s) - structural isomer , indazole , chemistry , crystal structure , structural motif , crystallization , stereochemistry , x ray crystallography , carboxylic acid , combinatorial chemistry , crystallography , diffraction , organic chemistry , biochemistry , physics , optics
Indazole is known as an important structural motif in medicinal chemistry and, recently, has also gained attention in other areas, such as materials chemistry, with many studies showing different potential applications for their regioisomers. Phosphonates are also a class of compounds with diverse applications, ranging from medicinal to material applications. Here we present the synthesis of 1 H ‐ and 2 H ‐indazolephosphonic acid derivatives substituted at C‐3, involving mono‐ or bisphosphonic acids, from their corresponding carboxylic acid and esters. These compounds were fully characterized, and their spectroscopic data were evaluated to identify and distinguish the structural scaffold of each phosphonic acid. Crystallization of [hydroxy(1‐methyl‐1 H ‐indazol‐3‐yl)methanediyl]bis(phosphonic acid) 7 afforded crystals suitable for single crystal X‐ray diffraction studies and its crystal structure details are also discussed.