title: Simple assembly of polysubstituted pyrazoles and isoxazoles via ring closure-ring opening domino reaction of 3-acyl-4,5-dihydrofurans with hydrazines and hydroxylamine.
abstract: A convenient general approach to 2-(pyrazol-4-yl)- and 2-(isoxazol-4-yl)ethanols based on the Brønsted acid-initiated reaction of 3-acyl-4,5-dihydrofurans with hydrazines or hydroxylamine was developed. Further transformation of the alcohol moiety in 2-(pyrazolyl)ethanols affording 2-(pyrazolyl)ethylamine as potent bioactive compounds as well as pyrazole-substituted derivatives of antitumor alkaloid crispine A was elaborated.
authors: Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russian Federation.
authors: Alexey O
authors: AO
authors: Chagarovskiy
authors: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, 1-3, Moscow 119991, Russian Federation. trush@phys.chem.msu.ru.
authors: Ekaterina M
authors: EM
authors: Budynina
authors: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, 1-3, Moscow 119991, Russian Federation. trush@phys.chem.msu.ru.
authors: Olga A
authors: OA
authors: Ivanova
authors: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, 1-3, Moscow 119991, Russian Federation. trush@phys.chem.msu.ru.
authors: Victor B
authors: VB
authors: Rybakov
authors: Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russian Federation and Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, 1-3, Moscow 119991, Russian Federation. trush@phys.chem.msu.ru.
authors: Igor V
authors: IV
authors: Trushkov
authors: Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory, 1-3, Moscow 119991, Russian Federation. trush@phys.chem.msu.ru.
authors: Mikhail Ya
authors: MY
authors: Melnikov
mesh_terms: D003500:Cyclization; D005663:Furans / Q000737:chemistry*; D006834:Hydrazines / Q000737:chemistry*; D019811:Hydroxylamine / Q000737:chemistry*; D007555:Isoxazoles / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011720:Pyrazoles / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D005663:Furans; D006834:Hydrazines; D007555:Isoxazoles; D011720:Pyrazoles; D019811:Hydroxylamine