Ayşe TAN, Mustafa Zahrittin KAZANCIOĞLU, Derya AKTAŞ, Özlem GÜNDOĞDU, Ertan ŞAHİN, Nurhan HORASAN KİSHALI, Yunus KARA

Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues

Three new polysubstituted isoindole-1,3-diones were prepared from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione. The reaction of 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione with m-CPBA gave the corresponding epoxide. The triacetate derivative was obtained via cis-hydroxylation using OsO4, followed by acetylation. An aromatic derivative, a secondary reaction product, was also formed during the acetylation. Finally, a tricyclic derivative from 2-ethyl-5-hydroxy-3a,4,5,7a-tetrahydro-isoindole-1,3-dione was synthesized via dichloroketene addition under microwave irradiation. The exact structures of epoxide and tricyclic derivatives were determined by X-ray diffraction analysis.

Anahtar Kelimeler:

Isoindole, norcantharimide, singlet oxygen, ketene, epoxidation

Convenient synthesis of new polysubstituted isoindole-1,3-dione analogues

Keywords:

Isoindole, norcantharimide, singlet oxygen, ketene, epoxidation,

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of all reflections with F
> 2 σ (F2) . Integration of the intensities, correction for Lorentz and polarization effects, and cell refinement were performed using CrystalClear (Rigaku/MSC Inc., 2005) software.20The structures were solved by direct methods using SHELXS-97
and refined by a full-matrix least-squares procedure also using SHELXL-97.21H atoms were positioned geometrically and refined using a riding model. The final difference Fourier maps showed no peaks of chemical significance. Crystal data for 8: C10H
NO4, crystal system, space group: monoclinic, P21/n; (no: 14); unit cell dimensions: a = 6.7632(2), b = 7.0863(3), c = 10.3539(4) ˚A, α = 97.172(5), β = 95.492(4), γ = 94.766(5) ˚A; volume: 487.81(3) ˚A3; Z = 2; calculated density: 1.438 g/cm3; absorption coefficient: 0.112 mm −1
; F(000): 224; θ -range for data collection 2.9–26.4; refinement method: ◦
full matrix least-square on F2; data/parameters: 1992/139; goodness-of-fit on F2: 1.051; final R-indices [I > 2 σ (I)]: R1= 0.066, wR2= 0.182; largest diff. peak and hole: 0.303 and –0.211 e ˚A −3
Crystal data for 12: C12H13NO3Cl2, crystal system, space group: monoclinic, P21/n; (no: 14); unit cell dimensions: a = 9.7024(3), b = 7.1974(3), c =18.6969(8) ˚
A, α = 90, β = 91.823(4), γ = 90 ˚A; volume: 1304.98(9) ˚3; Z = 4; A3; Z = 4; calculated density: 1.477 g/cm3; absorption coefficient: 0.496 mm −1
; F(000): 600; θ -range for data collection 2.2–26.5; refinement method: full matrix least-square on F2; data/parameters: 2670/164; goodness-of-fit on F2: 0.982; final R-indices [I > 2 σ (I)]: R1= 0.0703, wR2= 0.110; largest diff. peak and hole: 0.383 and –0.477 e ˚A −3 .
CCDC 938983 (8) and CCDC 939530 (12) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via
http://www.ccdc.cam.ac.uk/Community/Requestastructure/Pages/DataRequest.aspx? (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033; e-mail: deposit@ccdc.cam.ac.uk).