photoisomerization of ethyl 2–(3–acylselenoureido)thiophene– 3–carboxylates and their benzoanalogues光异构化的乙基2 -(3-acylselenoureido)噻吩- 3-carboxylates及其benzoanalogues.pdfVIP

Molecules 1997, 2, 135-151 molecules ISSN 1420-3049 Photoisomerization of Ethyl 2–(3–Acylselenoureido)thiophene– 3–carboxylates and Their Benzoanalogues 1,* 1 1 1 2 Pavel Pazdera , Jiri Sibor , Radek Marek , Michal Kuty and Jaromir Marek 1 2 Department of Organic Chemistry, Department of Inorganic Chemistry, Faculty of Science, Masaryk University, CZ–611 37 Brno, Czech Republic Tel.: +420 5 411 29 305; Fax: +420 5 412 112 14; E–mail: pazdera@chemi.muni.cz Received: 6 January 1997 / Accepted: 24 May 1997 / Published: 15 September 1997 Abstract: Synthesis, isomerisation and structure elucidation of the title compounds 1–6 and its isomers 7–12 1 13 15 77 by FTIR, H, C, N, Se NMR spectroscopy is reported. Ethyl 2–(3–acylselenoureido)thiophene–3– carboxylates and their benzoanalogues (where acyl is benzoyl and pivaloyl) were prepared by addition of ethyl 2–aminothiophene–3–carboxylates and ethyl 2–aminobenzoate on benzoyl– or pivaloylisoselenocyanate in acetone solution. An isomerization of 1–6 to the corresponding 3–acylisoselenoureas 7–12 was obtained. The isomerisation proceeds either by irradiation with light (340–400 nm) or in the case of benzoylderivatives 1, 3, 5 by treatment with acetic acid. On the other hand the acid action in the pivaloyl set inhibited this isomerisation and evoked the retroisomerisation reaction of 8, 10, 12 to 2, 4, 6. Thermal analyses showed that isomerisation can be init