TY - JOUR
T1 - Ring expansion reactions of 4-amino-1,1-dioxo-[1,2,3,5]-thiatriazoles
AU - Duggan, Peter J.
AU - Liepa, Andris J.
AU - O'Dea, Laura K.
AU - Tranberg, C. Elisabet
PY - 2007
Y1 - 2007
N2 - An unusual ring-expansion reaction of 4-amino-1,1-dioxo-[1,2,3,5]- thiatriazoles 4 has been identified that produces the relatively rare 5-amino-1,1-dioxo-[1,2,4,6]-thiatriazines 6 and 9. Initial alkylation of the thiatriazole 4 with α-halo-esters at N-3 produces α-substituted esters which, under basic reaction conditions, undergo opening of the thiatriazole ring and re-closure to a thiatriazine ring. Similar alkylations of 4 with diethyl chloromalonate and ethyl dichloroacetate lead to the loss of SO2 and the production of triazine 10a and triazole 14, apparently by an initial alkylation at N-5. The reaction of 4 with phenacyl bromides or a phenacyl dibromide forms fully unsaturated 5-amino-1,1-dioxo-[1,2,4,6]- thiatriazines 13.
AB - An unusual ring-expansion reaction of 4-amino-1,1-dioxo-[1,2,3,5]- thiatriazoles 4 has been identified that produces the relatively rare 5-amino-1,1-dioxo-[1,2,4,6]-thiatriazines 6 and 9. Initial alkylation of the thiatriazole 4 with α-halo-esters at N-3 produces α-substituted esters which, under basic reaction conditions, undergo opening of the thiatriazole ring and re-closure to a thiatriazine ring. Similar alkylations of 4 with diethyl chloromalonate and ethyl dichloroacetate lead to the loss of SO2 and the production of triazine 10a and triazole 14, apparently by an initial alkylation at N-5. The reaction of 4 with phenacyl bromides or a phenacyl dibromide forms fully unsaturated 5-amino-1,1-dioxo-[1,2,4,6]- thiatriazines 13.
UR - http://www.scopus.com/inward/record.url?scp=33846479900&partnerID=8YFLogxK
U2 - 10.1039/b615569c
DO - 10.1039/b615569c
M3 - Article
C2 - 17252129
AN - SCOPUS:33846479900
SN - 1477-0520
VL - 5
SP - 472
EP - 477
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 3
ER -