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Synthesis of sulfur containing analogues of the soluble guanylate cyclase inhibitor 8-bromo-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one NS2028

Berezin, Andrey A., Koutentis, Panayiotis A. and Manos, Manolis J. 2011. Synthesis of sulfur containing analogues of the soluble guanylate cyclase inhibitor 8-bromo-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazin-1-one NS2028. Tetrahedron 67 (30) , pp. 5437-5443. 10.1016/j.tet.2011.05.071

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Abstract

Sulfur analogues of the soluble guanylate cyclase (sGC) inhibitor NS2028 1a are synthesized. Treating 8-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one oxime (6) with 1,1′-thiocarbonyldiimidazole (1.1 equiv) gave the carbamothioate 8-bromo-4H-[1,2,4]oxadiazolo[3,4-c][1,4]benzoxazine-1-thione (3a) in 83% yield. Alternatively reacting NS2028 1a with P2S5 (0.5 equiv) affords the carbamothioate 3a in 80% yield. Similar treatment of 8-aryl substituted NS2028 analogues 1b–d with P2S5 gave the carbamothioates 3b–d in 64–91% yields. Although quite stable, the carbamothioates 3a–d could be thermally isomerized in the presence of Cu (10 mol %) to afford the thiocarbamates 4a–d in high yields. Interestingly, in the case of carbamothioate 3a Pd and In metals also facilitated the isomerization. Furthermore, treatment of the thiocarbamates 4a–d with P2S5 (0.5 equiv) affords the carbamodithioates 5a–d in 72–89% yields. All new compounds are fully characterized including single crystal X-ray data for carbamothioate 3a and thiocarbamate 4a. Finally, a mechanism is proposed for the carbamothioate to thiocarbamate isomerization.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Elsevier
ISSN: 0040-4020
Date of Acceptance: 16 May 2011
Last Modified: 20 Jan 2020 14:30
URI: http://orca-mwe.cf.ac.uk/id/eprint/128734

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