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Chemo‐ and Diastereoselective Synthesis of Pyrazolo‐tetrahydropyridines via Multicomponent Sequential Aza‐Diels‐Alder Reactions in Water
Author(s) -
Nazeri Mohammad Taghi,
Javanbakht Siamak,
Shaabani Ahmad,
Khavasi Hamid Reza
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201904172
Subject(s) - salicylaldehyde , phenylhydrazine , chemistry , intramolecular force , recrystallization (geology) , diels–alder reaction , solvent , organic chemistry , catalysis , stereochemistry , paleontology , schiff base , biology
In this study, we report a novel and an efficient strategy for the synthesis of chemo‐ and diastereoselective synthesis of pyrazolo‐tetrahydropyridines via a one‐pot multi‐component intramolecular Aza‐Diels–Alder reactions (ADARs) from benzoylacetonitrile derivatives, phenylhydrazine, salicylaldehyde derivatives, and styrenesulfonyl or cinnamoyl chloride in H 2 O as a green solvent. This synthesis procedure was also designed to follow the group‐assisted purification (GAP) chemistry, which can avoid traditional purification such as recrystallization and chromatography methods.