TY - JOUR
T1 - 2-Benzyliden-2H-thieto[3,2-b]quinoline
T2 - A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline
AU - Haddadin, Makhluf J.
AU - El-Nachef, Claudia
AU - Kisserwani, Hawraa
AU - Chaaban, Yara
AU - Kurth, Mark J.
AU - Fettinger, James C.
PY - 2010/12/22
Y1 - 2010/12/22
N2 - Synthesis of the strained 2H-thieto[3,2-b]quinoline ring system is reported for the first time. Treatment of (Z)-2-benzyliden-2H-thieto[3,2-b]quinoline derivatives of this heterocycle with base, at reflux in ethanol, causes a novel rearrangement to 2-phenylthieno[3,2-b]quinolines. Indeed, the one-pot reaction of 2-aminobenzaldehydes and (Z)-2-benzylidenethietan-3-one in refluxing basic ethanol leads directly to 2-phenylthieno[3,2-b]quinolines in good yields.
AB - Synthesis of the strained 2H-thieto[3,2-b]quinoline ring system is reported for the first time. Treatment of (Z)-2-benzyliden-2H-thieto[3,2-b]quinoline derivatives of this heterocycle with base, at reflux in ethanol, causes a novel rearrangement to 2-phenylthieno[3,2-b]quinolines. Indeed, the one-pot reaction of 2-aminobenzaldehydes and (Z)-2-benzylidenethietan-3-one in refluxing basic ethanol leads directly to 2-phenylthieno[3,2-b]quinolines in good yields.
KW - Base-mediated rearrangement
KW - Friedländer reaction
KW - Thieno[3,2-b]quinoline
KW - Thieto[3,2-b]quinoline
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U2 - 10.1016/j.tetlet.2010.10.039
DO - 10.1016/j.tetlet.2010.10.039
M3 - Article
AN - SCOPUS:78649320591
VL - 51
SP - 6687
EP - 6689
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 51
ER -