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Model Reactions for the Synthesis of Azacorannulenes and Related Heteroaromatic Compounds
Author(s) -
Dix Ina,
Doll Christian,
Hopf Henning,
Jones Peter G.
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(200208)2002:15<2547::aid-ejoc2547>3.0.co;2-a
Subject(s) - chemistry , isoquinoline , pyridine , quinoline , pyrolysis , medicinal chemistry , azulene , dimer , derivative (finance) , torr , organic chemistry , stereochemistry , physics , financial economics , economics , thermodynamics
Abstract 4‐(2‐Ethynylphenyl)pyridine ( 10 ), 3‐(2‐ethynylphenyl)pyridine ( 11 ), 2‐(2‐trimethylsilylethynylphenyl)pyridine ( 26 ), and 3‐ethynyl‐2‐phenylpyridine ( 13 ) were prepared from readily available pyridine precursors by standard coupling reactions. Pyrolysis of 10 at 810 °C/0.5 Torr provided benzo[ f ]isoquinoline ( 45 ) and the benzopentalene dimer 47 . Pyrolysis of 11 (820 °C/0.5 Torr) afforded benzo[ f ]quinoline ( 50 ), benzo[ h ]isoquinoline ( 52 ), and a mixture of isomers of 47 . Pyrolysis of 13 (820 °C/0.3 Torr) provided benzo[ h ]quinoline ( 56 ) and the novel azulene derivative azuleno[1,2‐ b ]pyridine ( 58 ). When 26 was desilylated by treatment with TBAF in THF/water, the unusual “dimerization” product 37 was produced; its structure was confirmed by X‐ray structural analysis. The mechanisms of these transformations are discussed. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)