TY - JOUR
T1 - Rhodium-Catalyzed Regioselective Synthesis of Isocoumarins through Benzothiadiazine-Fused Frameworks
AU - Dalvi, Prashant B.
AU - Lin, Kuang Ling
AU - Kulkarni, Manohar V.
AU - Sun, Chung-Ming
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/8/5
Y1 - 2016/8/5
N2 - An unprecedented two-step, one-pot synthesis of benzimidazothiadiazine 5,5-dioxides is presented. Reaction condition based regioselectivity has been achieved where fused benzimidazo[1,2-b][1,2,4]thiadiazines are exclusively formed under thermal conditions, whereas benzimidazo[2,1-c][1,2,4]thiadiazines were created only under microwave irradiation. The salient features of this protocol include a regioselective sulfonylation of 2-aminobenzimidazole with o-halo sulfonyl chlorides followed by N-C bond formation. The acid forms of these fused regioisomers have been used to introduce novel guanidine-containing isocoumarin frameworks.
AB - An unprecedented two-step, one-pot synthesis of benzimidazothiadiazine 5,5-dioxides is presented. Reaction condition based regioselectivity has been achieved where fused benzimidazo[1,2-b][1,2,4]thiadiazines are exclusively formed under thermal conditions, whereas benzimidazo[2,1-c][1,2,4]thiadiazines were created only under microwave irradiation. The salient features of this protocol include a regioselective sulfonylation of 2-aminobenzimidazole with o-halo sulfonyl chlorides followed by N-C bond formation. The acid forms of these fused regioisomers have been used to introduce novel guanidine-containing isocoumarin frameworks.
UR - http://www.scopus.com/inward/record.url?scp=84981250094&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.6b01408
DO - 10.1021/acs.orglett.6b01408
M3 - Article
AN - SCOPUS:84981250094
SN - 1523-7060
VL - 18
SP - 3706
EP - 3709
JO - Organic Letters
JF - Organic Letters
IS - 15
ER -