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

doi: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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

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 language	English (US)
Pages (from-to)	6687-6689
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	51
DOIs	https://doi.org/10.1016/j.tetlet.2010.10.039
State	Published - Dec 22 2010

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

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@article{4982364fac1941189105dafd9a98204a,

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

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.",

keywords = "Base-mediated rearrangement, Friedl{\"a}nder reaction, Thieno[3,2-b]quinoline, Thieto[3,2-b]quinoline",

author = "Haddadin, {Makhluf J.} and Claudia El-Nachef and Hawraa Kisserwani and Yara Chaaban and Kurth, {Mark J.} and Fettinger, {James C.}",

year = "2010",

month = dec,

day = "22",

doi = "10.1016/j.tetlet.2010.10.039",

language = "English (US)",

volume = "51",

pages = "6687--6689",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "51",

}

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

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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