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Updated: Jun 2, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Electrophile-driven regioselective synthesis of functionalized quinolines
Shaukat Ali1, Hai-Tao Zhu, Xiao-Feng Xia
1State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Chinese Academy of Science, Lanzhou, People's Republic of China.
A new method synthesizes highly substituted 3-iodoquinolines using 6-endo-dig iodocyclization. This efficient process yields up to 99% and allows for further functionalization of the resulting compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Heterocyclic Chemistry
Background:
- Quinolines are important heterocyclic compounds with diverse applications.
- Efficient synthesis of substituted quinolines remains a key challenge in organic chemistry.
Purpose of the Study:
- To develop a novel and efficient method for synthesizing highly substituted 3-iodoquinolines.
- To explore the regioselectivity and scope of the iodocyclization reaction.
Main Methods:
- The study employed a 6-endo-dig iodocyclization reaction.
- Reactants included 2-tosylaminophenylprop-1-yn-3-ols and molecular iodine (I(2)).
- The reaction was performed under mild conditions.
Main Results:
- Highly substituted 3-iodoquinolines were synthesized in moderate to excellent yields (up to 99%).
- The cyclization reaction demonstrated high regioselectivity.
- The synthesized 3-iodoquinolines are amenable to further functionalization via coupling reactions.
Conclusions:
- The developed 6-endo-dig iodocyclization provides an efficient route to diverse 3-iodoquinolines.
- This method offers a valuable tool for constructing complex quinoline derivatives.
- The resulting iodoquinolines serve as versatile intermediates for further chemical transformations.
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