caa a22 4500 467919895 CHVBK 20180406152914.0 cr unu---uuuuu 170328e20061001xx s 000 0 eng 10.1007/s00706-006-0536-7 doi (NATIONALLICENCE)springer-10.1007/s00706-006-0536-7 Synthesis of 1,2-Diazol-4-sulfonamides, 1,2,4- and 1,2,5-Oxadiazol-3-sulfonamides, 1,2,3-Triazol-4-sulfonamides, and Pyrimidine-5-sulfonamides starting from Cyanomethanesulfonyl Chloride [Elektronische Daten] [Martin Winterwerber, Rouzita Geiger, Hans-Hartwig Otto] Summary.: Cyanomethanesulfonyl chloride was reacted with amines yielding cyanomethanesulfonamides which could be transformed into alkoxymethylidene and aminomethylidene derivatives. The reaction of alkoxymethylidene derivatives with phenylhydrazine resulted in the formation of 5-aminopyrazol-4-sulfonamides, whereas from cyanomethanesulfonamides via the N-hydroxyamidine derivatives and their reaction with esters 1,2,4-oxadiazol-3-methanesulfonamides became accessible. Nitrosation of cyanomethanesulfonamides yielded 2-hydroxyimino derivatives which were then transformed into 2-hydroxyimino N-hydroxyamidine derivatives, and finally cyclized into 4-amino-1,2,5-oxadiazol-3-sulfonamides. On the other hand diazotation of cyanomethanesulfonamides gave the 2-arylhydrazono derivatives, which after transformation into N-hydroxyamidine derivatives gave by reaction with POCl3 5-amino-1,2,3-triazol-4-sulfonamides. Finally, the reaction between cyanomethanesulfonamides and formamidinium acetate opened an easy access to 4-aminopyrimidine-5-sulfonamides, which could be transformed by trialkyl orthoformiates into substituted pyrimidino[4,5-e][1,2,4]thiadiazine derivatives. All intermediates as well as transformation products of the heterocyclic systems were isolated and well characterized. Mechanisms were discussed, and the stereochemistry, when necessary and possible, was elucidated. Springer-Verlag, 2006 Keywords. Cyanomethanesulfonyl chloride nationallicence 1,2-Diazol-4-sulfonamides nationallicence Oxadiazol-3-sulfonamides nationallicence 1,2,3-Triazol-4-sulfonamides nationallicence Pyrimidine-5-sulfonamides nationallicence Winterwerber Martin Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany aut Geiger Rouzita Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany aut Otto Hans-Hartwig Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/10(2006-10-01), 1321-1347 0026-9247 137:10<1321 2006 137 706 https://doi.org/10.1007/s00706-006-0536-7 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0536-7 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Winterwerber Martin Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany aut NATIONALLICENCE 700 1- Geiger Rouzita Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany aut NATIONALLICENCE 700 1- Otto Hans-Hartwig Department of Pharmaceutical/Medicinal Chemistry (PMC), Institute of Pharmacy, Ernst-Moritz-Arndt-University Greifswald, Greifswald, Germany aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/10(2006-10-01), 1321-1347 0026-9247 137:10<1321 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer