A versatile route to 3-benzoheteroepines containing group 15 and 16 heavier elements involving several novel ring systems, and their thermal stabilities.
The C-unsubstituted 3-benzoheteroepines (2a-g) containing group 15 (P, As, Sb, and Bi) and group 16 (S, Se, and Te) heavier elements were prepared by the reaction of the corresponding metal reagents with (Z,Z)-o-bis(beta-lithiovinyl)benzene (5) which was derived in two steps from a common o-phthalaldehyde (3). The heteroepines (2) thus obtained were thermally labile towards heteroatom extrusion, and their half-lives on heating estimated from (1)H-NMR spectral analysis showed that the 3-benzoheteroepines (2) were far less stable than the corresponding 1-benzoheteroepines (1). The 2,4-bis(trimethylsilyl)-3-benzoheteroepines (17) containing Sb, Bi, and Te were also prepared from o-diiodobenzene (9) in 6 steps and were found to be more stable than the corresponding C-unsubstituted heteroepines (2).
Yasuike
Shuji
S
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.
Kiharada
Tsutomu
T
Tsuchiya
Takashi
T
Kurita
Jyoji
J
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004355:Drug Stability; D006207:Half-Life; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D019216:Metals, Heavy / Q000737:chemistry*; D013696:Temperature; D013816:Thermodynamics; D009764:o-Phthalaldehyde
D006574:Heterocyclic Compounds, 2-Ring; D007202:Indicators and Reagents; D019216:Metals, Heavy; D009764:o-Phthalaldehyde