Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via α-ferrocenyl carbenium ions as key intermediates

TETRAHEDRON

卷:73

Article

Minic, Aleksandra¹  Stevanovic, Dragana¹  Vukicevic, Mirjana²  Bogdanovic, Goran A.³  D'hooghe, Matthias⁴  Radulovic, Niko S.⁵  Vukicevic, Rastko D.¹ 

[1] Univ Kragujevac, Dept Chem, Fac Sci, R Domanovica 12, Kragujevac 34000, Serbia

[2] Univ Kragujevac, Dept Pharm, Fac Med Sci, S Markovica 69, Kragujevac 34000, Serbia

[3] Univ Belgrade, Vinca Inst Nucl Sci, POB 522, Belgrade 11001, Serbia

[4] Univ Ghent, Fac Biosci Engn, Dept Sustainable Organ Chem & Technol, Coupure Links 653, B-9000 Ghent, Belgium

[5] Univ Nis, Fac Sci & Math, Dept Chem, Visegradska 33, Nish 18000, Serbia

关键词: alpha-Ferrocenyl carbenium ion;    Quinolines;    Tetrahydroquinolines;    DDQ aromatization;    Intramolecular cyclization;   

DOI  :  10.1016/j.tet.2017.09.014

来源: Elsevier

【 摘 要 】

A series of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines were synthesized in high-to-excellent yields (up to 99%) starting from the corresponding ferrocenoylethyl aryl amines. These Mannich bases were reduced (NaBH4) to the corresponding 3-(arylamino)-1-ferrocenylpropan-1-ols and submitted to an intramolecular cyclization prompted by acetic acid, proceeding via the corresponding alpha-ferrocenyl carbenium ion intermediates. Subsequently, the obtained tetrahydroquinolines were smoothly oxidized (aromatized) by means of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to provide the corresponding 4-ferrocenylquinolines (up to 93%). (C) 2017 Elsevier Ltd. All rights reserved.

【 授权许可】

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