Three-Component Diastereoselective Synthesis of Stable 1,4-Diionic Organosulfurs

Abstract

The simple and efficient diastereoselective synthesis of stable 1,4-diionic organosulfur derivatives by the three-component reaction of dialkyl acetylenedicarboxylates, elemental sulfur, and N-heteroaromatic compounds is reported.

Key words

acetylenic ester - 1,4-diionic organosulfur - pyridine - elemental­ sulfur

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15

X-ray data for 4h: (C₁₃H₁₅NO₄S), M = 281.33 g/mol, monoclinic system, space group P2₁/c, a = 10.5164 (8), b = 16.3854 (12), c = 8.1277 (6) Å, β = 91.46˚, V = 1400.08 (18) Å^³, Z = 4, Dc = 1.335 g cm^-³, µ(MoKα radiation) = 0.240 mm^-¹, crystal dimension of 0.36 × 0.35 × 0.25 mm. The structure was solved by using SHELXL-97. The structure refinement and data reduction was carried out with X-Area 1.31 programs.^¹6 The non-hydrogen atoms were refined anisotropically by full matrix least-squares on F ^² values to final R ₁ = 0.0425, wR ₂ = 0.1215, and S = 1.026 with 172 parameters using 3759 independent reflections (θ range = 2.30-29.17˚). Hydrogen atoms were located from expected geometry and were not refined. Crystallographic data for 4h have been deposited with the Cambridge Crystallographic Data Centre. Copies of the data can be obtained, free of charge, on application to The Director, CCDC 789416, Union Road, Cambridge CB2 1EZ, UK. Fax: [phone] or e-mail: [e-mail].