caa a22 4500 467920559 CHVBK 20180406152916.0 cr unu---uuuuu 170328e20061101xx s 000 0 eng 10.1007/s00706-006-0541-x doi (NATIONALLICENCE)springer-10.1007/s00706-006-0541-x Reactions of Cyanomethanesulfonamides with Aldehydes and Synthesis of 2-Benzyl-2,3-dihydrobenzopyrano[3,2- e ] [1,2,4]thiadiazine 1,1-Dioxides [Elektronische Daten] [Martin Winterwerber, Rouzita Geiger, Ursula Predoiu, Hans-Hartwig Otto] Summary.: Reactions of cyanomethanesulfonamides with aromatic aldehydes in the presence of AcOH and piperidine produced the addition products, the 1-cyano-2-arylethenesulfonamides, whereas reactions with benzonitrile yielded the 2-amino-1-cyano-2-phenylethenesulfonamides only when done in THF with BuLi. No addition products were isolated from the analogue reactions with 2-hydroxybenzaldehyde (salicylaldehyde). Instead, we obtained 2-imino-2H-chromene-3-sulfonamides with good to excellent yields. These 2H-chromene derivatives allowed a number of transformations, from which the reactions with orthoformates opened an approach to the hitherto unknown benzopyrano[3,2-e] [1,2,4]thiadiazine ring system. Springer-Verlag, 2006 Keywords. Cyanomethanesulfonamide nationallicence Aldehyde nationallicence Condensation nationallicence Cyclization nationallicence Benzopyrano[3,2- e ] [1,2,4]thiadiazine 1,1-dioxide nationallicence Winterwerber Martin Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany aut Geiger Rouzita Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany aut Predoiu Ursula Institute of Pharmacy, University of Freiburg, Freiburg, Germany aut Otto Hans-Hartwig Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/11(2006-11-01), 1441-1451 0026-9247 137:11<1441 2006 137 706 https://doi.org/10.1007/s00706-006-0541-x text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00706-006-0541-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Winterwerber Martin Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany aut NATIONALLICENCE 700 1- Geiger Rouzita Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany aut NATIONALLICENCE 700 1- Predoiu Ursula Institute of Pharmacy, University of Freiburg, Freiburg, Germany aut NATIONALLICENCE 700 1- Otto Hans-Hartwig Department of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, Greifswald, Germany aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 137/11(2006-11-01), 1441-1451 0026-9247 137:11<1441 2006 137 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer