Synthesis of Spiro[indole-3,3′-pyrrolidine]-2′-(thi)ones

被引：7

作者：

Yasui, Motohiro ^{[1
]}

Ohbu, Haruna ^{[1
]}

Ishikawa, Maho ^{[1
]}

Yoshida, Tatsuhito ^{[1
]}

Takeda, Norihiko ^{[1
]}

Hirao, Seiya ^{[2
]}

Abe, Takumi ^{[2
]}

Ueda, Masafumi ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Kobe 6588558, Japan

[2] Okayama Univ, Grad Sch Med Dent & Pharmaceut Sci, Okayama 7008530, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 02期

关键词：

CHEMICAL SPACE; INDOLES; DEAROMATIZATION; DIVERSITY;

D O I：

10.1021/acs.joc.2c02561

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Spiro[indole-3,3 '-pyrrolidine]-2 '-ones were synthesized via one-pot chloroformylation-dearomatizing spirocyclization of tryptamine derivatives. Moreover, the thio equivalent spiro[indole-3,3 '-pyrrolidine]-2 '-thiones, for which the synthesis and properties were previously unreported, were synthesized. The procedures are easily implemented, have a broad scope, and are transition-metal-free and cheap. To demonstrate the utility of the synthetic methodology, the spiro[indole-3,3 '-pyrrolidine]-2 '-ones were converted into heterocyclic scaffolds, such as an optically active spiroindoline and spirooxindole.

引用

页码：1093 / 1106

页数：14

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