A novel dilithiation approach to 3,4-dihydro-2H-1,3-benzothiazines, 3,4-Dihydro-2H-1,3-benzoxazines, and 2,3,4,5-tetrahydro-1,3-benzothiazepines.
3,4-Dihydro-2H-1,3-benzothiazines 4, 3,4-dihydro-2H-1,3-benzoxazines 9, and 2,3,4,5-tetrahydro-1,3-benzothiazepines 6 were synthesized by directed ortho-lithiation of thiophenols and phenols and by side-chain lithiation of substituted thiophenols, respectively, in one-pot by reacting with N,N-bis[(benzotriazol-1-yl)methyl]amines 3 as 1,3-biselectrophile synthons.
Katritzky
Alan R
AR
Center for Heterocyclic Chemistry, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA. katritzky@chem.ufl.edu
Xu
Yong-Jiang
YJ
Jain
Ritu
R
D002491:Central Nervous System Agents / Q000138:chemical synthesis; D002626:Chemistry, Pharmaceutical; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry; D010078:Oxazines / Q000138:chemical synthesis; D013841:Thiazepines / Q000138:chemical synthesis; D013843:Thiazines / Q000138:chemical synthesis
D002491:Central Nervous System Agents; D006574:Heterocyclic Compounds, 2-Ring; D010078:Oxazines; D013841:Thiazepines; D013843:Thiazines; D008094:Lithium