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Nitrogen bridgehead compounds. Part 77 . Addition reaction of 9‐methylene‐6,7,8,9‐tetrahydro‐4 H ‐pyrido[1,2‐ a ]pyrimidin‐4‐ones
Author(s) -
Tóth Gábor,
Janke Frank,
Hermecz István,
Bitter István
Publication year - 1990
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.5570270225
Subject(s) - chemistry , diastereomer , epimer , stereoselectivity , methylene , bromine , stereochemistry , nitrogen , medicinal chemistry , organic chemistry , catalysis
Addition of bromine or thioacetic acid onto 6‐methyl‐9‐methylenetetrahydro‐4 H ‐pyrido[1,2‐ a ]pyrimidin‐4‐ones is stereoselective and gives the cis 6‐Me,9‐CH substituted products. Addition is also stereoselective in respect to the C(9) and C(10) centers, and gives as the primary product the erythro diastereomer, which may then undergo epimerization to the threo isomer. Relative configuration and predominant conformation of the products were determined by 1D and 2D nmr methods.