One-pot synthesis of benzothiazolines and napthathiazolines via cascade ortho-lithiation, cyclisation and elimination of N-arylsulfonyl lactams.
ortho-Lithiation of cyclic aryl sulfonamides in the presence of phosphoryl chloride provides a very simple entry to fused polycyclic sultams (benzothiazolines and naphthathiazolines).
Harling
John D
JD
GlaxoSmithKline, Gunnels Wood Road, Stevenage, Herts, UK SG1 2NY.
Steel
Patrick G
PG
Woods
Tom M
TM
Yufit
Dmitry S
DS
D052160:Benzothiazoles / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007769:Lactams / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*
D052160:Benzothiazoles; D007769:Lactams; D009281:Naphthalenes; D013451:Sulfonic Acids; C058836:benzothiazoline; D008094:Lithium