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One‐Pot Synthesis of 2‐(Alkylsulfanyl)quinolines from Aryl Isothiocyanates and Allenes or Alkynes Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2024, Article number : e202400033, Pages count : DOI: 10.1002/ejoc.202400033
Tags 2-(alkylsulfanyl)quinolines; N-aryl-1-aza-1,3,4-trienes; aryl isothiocyanates; allenesand alkynes; electrocyclization
Authors Nedolya Nina 1 , Tarasova Olga 1 , Artem’ev Alexander 2 , Albanov Alexander 1 , Bagryanskaya Irina 3 , Trofimov Boris A. 1
Affiliations
1 An Unsaturated Heteroatom Compounds Laboratory A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences 1, Favorsky Str., 664033 Irkutsk, Russian Federation E-mail: nina@irioch.irk.ru, boris_trofimov@irioch.irk.ru
2 Laboratory of Metal-Organic Coordination Polymers A. V. Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences 3, Acad. Lavrentiev Ave., 630090 Novosibirsk, Russian Federation E-mail: chemisufarm@yandex.ru
3 Spectral Research Center, N. N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences 9, Akad. Lavrentiev Ave., 630090 Novosibirsk, Russian Federation E-mail: bagryan@nioch.nsc.ru

Abstract: Abstract In this work, a conceptually novel approach to diversely substituted 2-(alkylsulfanyl)quinolines is described. The approach includes the assembly of the target molecules from allenic or acetylenic carbanions, aromatic isothiocyanates, and alkylating agents, The process proceeds in a single synthetic operation via the formation and 6π-electrocyclization of N-aryl-1-aza-1,3,4-trienes, R2R3C=C=C(R1)C(SAlk)=NAr, with the participation of the carbon-carbon double bond of the phenyl group and the azadiene fragment of the azatrienic system.
Cite: Nedolya N. , Tarasova O. , Artem’ev A. , Albanov A. , Bagryanskaya I. , Trofimov B.A.
One‐Pot Synthesis of 2‐(Alkylsulfanyl)quinolines from Aryl Isothiocyanates and Allenes or Alkynes
European Journal of Organic Chemistry. 2024. e202400033 . DOI: 10.1002/ejoc.202400033 WOS
Dates:
Submitted: Jan 11, 2024
Accepted: Feb 28, 2024
Published online: Feb 28, 2024
Identifiers:
Web of science WOS:001186283400001
OpenAlex W4392288633
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