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

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

Журнал

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Вых. Данные

Год: 2024, Том: 27, Номер: 13, Номер статьи : e202400033, Страниц : DOI: 10.1002/ejoc.202400033

Ключевые слова

2-(alkylsulfanyl)quinolines; N-aryl-1-aza-1,3,4-trienes; aryl isothiocyanates; allenesand alkynes; electrocyclization

Авторы

Nedolya Nina ¹ , Tarasova Olga ¹ , Artem’ev Alexander ² , Albanov Alexander ¹ , Bagryanskaya Irina ³ , Trofimov Boris A. ¹

Организации

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 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.

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. V.27. N13. e202400033 . DOI: 10.1002/ejoc.202400033 WOS OpenAlex

Поступила в редакцию:	11 янв. 2024 г.
Принята к публикации:	28 февр. 2024 г.
Опубликована online:	28 февр. 2024 г.

Web of science:	WOS:001186283400001
OpenAlex:	W4392288633

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