Unexpected Nucleophilic Participation and Rearrangement of DBU in Reactions with Saccharin Derivatives

Abstract

DBU attacks saccharin derivatives with subsequent rearrangement to give rise to 3-[3′-(1′′-azepin-2′′-onyl)propylamino]-1,2-benzisothiazole-1,1-dioxide 2 after work-up.

Keywords:

• DBU
• Nucleophile

Acknowledgment

This investigation has enjoyed the support of Payame Noor University, Iran.

Notes

^aMolecular formula C₁₆H₂₁N₃O₃S (M_r = 335.42), crystal size 0.200 × 0.200 × 0.450 mm³, monoclinic, space group P2₁/c, a = 8.463(7) A°, b = 16.475 (9) A°, c = 11.835 (7) A°, V = 1646 (2) A°³, Z = 4, D = 1.354 g cm⁻³, μ(MoKα) = 2.05 cm⁻¹, F ₀₀₀ = 712.2997 Unique reflections collected on a Rigaku AFC6S sequential diffractometer, 2θ_max = 50.0°. The structure was solved by direct methods and H atoms were placed geometrically and allowed to ride on the relevant non-H atom. Refinement coverged to give R = 0.061 and R _w  = 0.069.