One-Pot Synthesis of 2-Sulfonamidobenzo[b]thiophenes Enabled by a Mild Protonative Activation of Ynamides

Solbin Kim; So Yeun Lim; Kihun Kwak; Hee Nam Lim; Hyun-Suk Yeom

doi:10.1055/a-1929-2650

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(24): 5451-5460
DOI: 10.1055/a-1929-2650

paper

One-Pot Synthesis of 2-Sulfonamidobenzo[b]thiophenes Enabled by a Mild Protonative Activation of Ynamides

Solbin Kim

^aEco-Friendly New Materials Research Center, Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon, 34114, Republic of Korea

^bDepartment of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul, 04763, Republic of Korea

,

So Yeun Lim

^aEco-Friendly New Materials Research Center, Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon, 34114, Republic of Korea

^bDepartment of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul, 04763, Republic of Korea

,

Kihun Kwak

^aEco-Friendly New Materials Research Center, Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon, 34114, Republic of Korea

^bDepartment of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul, 04763, Republic of Korea

,

Hee Nam Lim ∗

^cDepartment of Chemistry and Biochemistry, Yeungnam University, 280 Daehak-Ro, Gyeongsan, Gyeongbuk, 38541, Republic of Korea

,

Hyun-Suk Yeom∗

^aEco-Friendly New Materials Research Center, Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology (KRICT), 141 Gajeong-ro, Yuseong-gu, Daejeon, 34114, Republic of Korea

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Abstract

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Abstract

The silica gel promoted or solvent-promoted protonative intramolecular cyclization of ynamides containing an o-(methylthio)aryl group resulted in the one-pot formation of biologically important benzo[b]thiophenes. Compared with ynamide activation methods that use strong Brønsted acids or expensive transition metals, this protocol is mild and economical. Due to these merits, various functionalized 2-amidobenzo[b]thiophenes were furnished in a convenient way.

Key words

ynamides - one pot - electrophilic cyclization - benzo[b]thiophenes - silica gel assisted

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Referenzen

References

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