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Synlett 2018; 29(20): 2707-2711
DOI: 10.1055/s-0037-1609655
letter
© Georg Thieme Verlag Stuttgart · New York

A Novel One-Pot, Two-Step Reaction for the Synthesis of Indenopyrrolo[3,2-c]pyridinone Derivatives with a Recyclable Catalyst

Chunmei Li
,
Furen Zhang*
School of Chemistry and Chemical Engineering, Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang Province 312000, P. R. of China   Email: frzhang@usx.edu.cn
,
Chenze Qi
› Author AffiliationsWe are grateful for financial support from the Open Research Foundation of Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process.
Further Information

Publication History

Received:13.09.2018

Accepted after revision: 16 October 2018

Publication Date:
14 November 2018 (online)

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Abstract

An efficient strategy was developed for the synthesis of indenopyrrolopyridinone derivatives from 4-hydroxy-6-methyl-2H-pyran-2-one, an amine, and 2,2-dihydroxy-1H-indene-1,3(2H)-dione by a one-pot, two-step, four-component process. The one-pot reaction gives various substituted indenopyrrolopyridinones in good yields and uses a solid acid as a recyclable catalyst in water. This procedure has the advantages of inexpensive substrates, a reusable solid-supported catalyst, and a convenient one-pot operation.

Key words

multicomponent reaction - one-pot reaction - hydroxy­methylpyranonone - amines - dihydroxyindenedione - indenopyrrolopyridinones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609655.
  • Supporting Information
 

  • References and Notes

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  • 17 2,5-Disubstituted 5a,10a-Dihydroxy-3-methyl-2,5,5a,10a-tetrahydroindeno[2′,1′:4,5]pyrrolo[3,2-c]pyridine-1,10-diones 5a–l; General Method A mixture of pyranone 1 (0.5 mmol), the appropriate amine 2 (1.0 mmol), and solid acid (10 mg) in H2O (3.0 mL) in sealed tube was heated at 80 °C until starting material was completely converted (~2 h; TLC). Indenedione 4 (0.5 mmol) was then added and the mixture was heated at 80 °C for another 4 h. The mixture was cooled to r.t. and the solid product was collected by filtration and washed with H2O. The crude product and solid acid were treated with hot 95% EtOH. The catalyst was removed by filtration, and the pure product 5 was obtained from the mother liquor. 5a,10a-Dihydroxy-3-methyl-2,5-diphenyl-2,5,5a,10a-tetrahydroindeno[2′,1′:4,5]pyrrolo[3,2-c]pyridine-1,10-dione (5a) Yellow crystals; yield: 177.0 mg (81%); mp 238–240 °C. IR (KBr): 3403, 1721, 1638, 1487, 1454, 1357, 1197, 1021, 943, 870, 772 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.85–7.86 (m, 1 H, ArH), 7.39–7.52 (m, 10 H, ArH), 7.20–7.23 (m, 1 H, ArH), 7.11–7.14 (m, 1 H, ArH), 6.78 (dd, J = 5.6, 2.8 Hz, 1 H, ArH), 6.41 (br s, 1 H, OH), 5.63 (s, 1 H, CH), 5.36 (s, 1 H, OH), 1.83 (s, 3 H, CH3). 13C NMR (100 MHz, CDCl3): δ = 197.3, 161.2, 155.9, 150.7, 147.7, 138.3 (2 C), 136.9, 135.2 (2 C), 135.0, 129.9, 129.4, 128.8, 128.7, 128.5, 128.4, 127.8 (2 C), 124.9, 124.5, 100.2, 96.2, 93.4, 82.7, 77.3, 22.5. HRMS (ESI): m/z [M + H]+ calcd for C27H21N2O4 +: 437.1496; found: 437.1495.
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