Premium
Reductive Cleavage of Potential Cholinomimetics Thiadiazolidinones: A New Family of Spiro Compounds
Author(s) -
Martinez Ana,
Alonso Diana,
Castro Ana,
GutierrezPuebla Enrique,
Baños JosepEladí,
Badia Albert
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200002)2000:4<675::aid-ejoc675>3.0.co;2-6
Subject(s) - chemistry , piperidine , stereochemistry , cleavage (geology) , nuclear magnetic resonance spectroscopy , triazine , muscarinic acetylcholine receptor , combinatorial chemistry , organic chemistry , receptor , biochemistry , geotechnical engineering , fracture (geology) , engineering
The design, synthesis and evaluation of a series of 1,2,4‐thiadiazolidinones with potential muscarinic receptor binding properties has been performed. During the synthesis of the target compounds, we observed an interesting reductive cleavage of the thiadiazolidinone system which leads to the formation of the novel piperidine spiro triazine heterocycle. The synthesis, structural elucidation (NMR spectroscopy and X‐ray diffraction) and biological evaluation of the new compounds are described. With the structures unequivocally established, a mechanism for the formation of the spiro compound is proposed.