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

共 50 条

[1] Synthesis of novel spiro[indole-3,3′-pyrrolidin]-2(1H)-ones
G. A. Gazieva
N. G. Kolotyrkina
A. N. Kravchenko
N. N. Makhova
Russian Chemical Bulletin, 2014, 63 : 431 - 434
[2] Synthesis of novel spiro[indole-3,3′-pyrrolidin]-2(1H)-ones
Gazieva, G. A.
Kolotyrkina, N. G.
Kravchenko, A. N.
Makhova, N. N.
RUSSIAN CHEMICAL BULLETIN, 2014, 63 (02) : 431 - 434
[3] Rapid and facile synthesis of spiro[indole-3,3′-[1,2,4]triazol]-2(1H)-ones
Mohamed, Ashraf M.
Alsharari, Musaed A.
Aly, Ashraf A.
JOURNAL OF CHEMICAL RESEARCH, 2010, (04) : 200 - 202
[4] STUDIES IN SPIRO HETEROCYCLES .4. INVESTIGATION OF THE REACTIONS OF FLUORINATED 3-AROYLMETHYLENE-INDOL-2-ONES WITH HYDRAZINE AND PHENYLHYDRAZINE AND SYNTHESIS OF SPIRO [INDOLE-3,3'-PYRAZOL]-2-ONES
JOSHI, KC
JAIN, R
GARG, S
PHARMAZIE, 1985, 40 (01): : 21 - 22
[5] Intramolecular Mannich reaction of 2-oxotryptamines with acetone yielding spiro[indole-3,3′-pyrrolidin]-2-ones
Incze, M
Dörnyei, G
Kajtár-Peredy, M
Szántay, C
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1999, 64 (02) : 408 - 416
[6] Copper-Catalyzed Trifluoromethylation of Acrylamides Coupled with Indole Dearomatization: Access to Trifluoromethyl-Substituted Spiro[indole-3,3′-pyrrolidine] Derivatives
Han, Guifang
Wang, Qiang
Chen, Linwei
Liu, Yuxiu
Wang, Qingmin
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (04) : 561 - 566
[7] Direct Synthesis of Sulfonylated Spiro[indole-3,3′-pyrrolidines] by Silver-Mediated Sulfonylation of Acrylamides Coupled with Indole Dearomatization
Dong, Wei
Qi, Lin
Song, Jin-Yan
Chen, Jia-Min
Guo, Jia-Xin
Shen, Song
Li, Li-Jun
Li, Wei
Wang, Li-Jing
ORGANIC LETTERS, 2020, 22 (05) : 1830 - 1835
[8] Synthesis of spiro[indole-3,3'-[1,3,4]thiadiazino[3,2-a]benzimidazoles] and spiro[indole-3,6'-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines]
Gaponenko, N. I.
Kolodina, A. A.
Lesin, A. V.
Kurbatov, S. V.
Starikova, Z. A.
Nelyubina, Yu. V.
RUSSIAN CHEMICAL BULLETIN, 2010, 59 (04) : 838 - 844
[9] Synthesis of Selenylated Spiro[indole-3,3′-quinoline] Derivatives via Visible-Light-Promoted Isocyanide Insertion
Liu Haoyang
Sun Shuangshuang
Ma Xianli
Chen Yanyan
Xu Yanli
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (09) : 2867 - 2876
[10] A convenient synthetic route to spiro[indole-3,4′-piperidin]-2-ones
Freund, R
Mederski, WWKR
HELVETICA CHIMICA ACTA, 2000, 83 (06) : 1247 - 1255

← 1 2 3 4 5 →