2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline

Makhluf J. Haddadin, Claudia El-Nachef, Hawraa Kisserwani, Yara Chaaban, Mark J. Kurth, James C. Fettinger

Research output: Contribution to journal › Article

4 Citations (Scopus)

Abstract

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.

Original languageEnglish (US)
Pages (from-to)6687-6689
Number of pages3
JournalTetrahedron Letters
Volume51
Issue number51
DOIs
StatePublished - Dec 22 2010

Fingerprint

Quinolines
Ethanol
Derivatives
quinoline
2-aminobenzaldehyde

Keywords

  • Base-mediated rearrangement
  • Friedländer reaction
  • Thieno[3,2-b]quinoline
  • Thieto[3,2-b]quinoline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Haddadin, M. J., El-Nachef, C., Kisserwani, H., Chaaban, Y., Kurth, M. J., & Fettinger, J. C. (2010). 2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline. Tetrahedron Letters, 51(51), 6687-6689. https://doi.org/10.1016/j.tetlet.2010.10.039

2-Benzyliden-2H-thieto[3,2-b]quinoline : A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline. / Haddadin, Makhluf J.; El-Nachef, Claudia; Kisserwani, Hawraa; Chaaban, Yara; Kurth, Mark J.; Fettinger, James C.

In: Tetrahedron Letters, Vol. 51, No. 51, 22.12.2010, p. 6687-6689.

Research output: Contribution to journal › Article

Haddadin, MJ, El-Nachef, C, Kisserwani, H, Chaaban, Y, Kurth, MJ & Fettinger, JC 2010, '2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline', Tetrahedron Letters, vol. 51, no. 51, pp. 6687-6689. https://doi.org/10.1016/j.tetlet.2010.10.039
Haddadin MJ, El-Nachef C, Kisserwani H, Chaaban Y, Kurth MJ, Fettinger JC. 2-Benzyliden-2H-thieto[3,2-b]quinoline: A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline. Tetrahedron Letters. 2010 Dec 22;51(51):6687-6689. https://doi.org/10.1016/j.tetlet.2010.10.039
Haddadin, Makhluf J. ; El-Nachef, Claudia ; Kisserwani, Hawraa ; Chaaban, Yara ; Kurth, Mark J. ; Fettinger, James C. / 2-Benzyliden-2H-thieto[3,2-b]quinoline : A new heterocycle and its rearrangement to 2-phenylthieno[3,2-b]quinoline. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 51. pp. 6687-6689.
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abstract = "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.",
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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.

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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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