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Reactions of Pyridine Analogues of Aza‐ o ‐xylylenes Generated from 1,3‐Dihydroisothiazolo[4,3‐ b ]pyridine 2,2‐Dioxides (Pyridosultams) − Formation of 2:1 Adducts with N ‐Phenylmaleimide
Author(s) -
Wojciechowski Krzysztof,
Kosinski Szymon
Publication year - 2002
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 - 10.1002/1099-0690(200203)2002:5<947::aid-ejoc947>3.0.co;2-n
Subject(s) - chemistry , pyridine , adduct , medicinal chemistry , stereochemistry , organic chemistry
Pyridine analogues 16−20 of aza‐ o ‐xylylenes, generated from pyridosultams 11−15 , enter into Diels−Alder reactions with dienophiles to form 1,2,3,4‐tetrahydronaphthyridines 23−28 , which then add another equivalent of a dienophile to form 2:1 adducts 29−36 . Intramolecular Diels−Alder reactions of aza‐ o ‐xylylenes 45 and 46 , generated from pyridosultams 43 and 44 , produced tricyclic pyrrolo‐ and pyridonaphthyridines 47 and 48 , which were used for the construction of the 10,14‐diazasteroid frameworks 52 and 54 . (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)