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Regioselective Diastereomeric Michael Adducts as Building Blocks in Heterocyclic Synthesis
Author(s) -
ElHashash Maher A.,
Rizk Sameh A.
Publication year - 2016
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2375
Subject(s) - chemistry , regioselectivity , adduct , steric effects , nucleophile , diastereomer , reagent , michael reaction , pyridine , nucleophilic addition , organic chemistry , stereochemistry , catalysis
The reaction of 4‐(4‐acetylamino/bromophenyl)‐4‐oxobut‐2‐enoic acids with carbon nucleophiles afforded Michael adducts depending on the type of nucleophilic reagents and medium (acidic or basic). The adducts 2 and 3 were used as key starting materials to synthesize some heterocyclic compounds, which include pyridazinone, furanone, 1,2‐oxazin‐5‐one, 1.2‐diazapine, pyrane, and hydroxyl pyridine derivatives. The Steric factor plays an important role in regioselectivity. The structure of newly synthesized compounds was elucidated by elemental analysis and spectroscopic data.