Oxidation Strategy for the Synthesis of Regioisomeric Spiroisobenzofuranopyrroles: Facile Entries to Spiro[isobenzofuran-1,2′-pyrrole] and Spiro[isobenzofuran-1,3′-pyrrole] Derivatives

Yefeng Fan; Song Liu; Nanyang Chen; Xusheng Shao; Xiaoyong Xu; Zhong Li

doi:10.1055/s-0034-1379617

Synlett, Table of Contents

Synlett 2015; 26(03): 393-403
DOI: 10.1055/s-0034-1379617

letter

Oxidation Strategy for the Synthesis of Regioisomeric Spiroisobenzofuranopyrroles: Facile Entries to Spiro[isobenzofuran-1,2′-pyrrole] and Spiro[isobenzofuran-1,3′-pyrrole] Derivatives

Authors

Yefeng Fan

^aShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China Email: shaoxusheng@ecust.edu.cn Email: lizhong@ecust.edu.cn
Song Liu

^aShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China Email: shaoxusheng@ecust.edu.cn Email: lizhong@ecust.edu.cn
Nanyang Chen

^aShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China Email: shaoxusheng@ecust.edu.cn Email: lizhong@ecust.edu.cn
Xusheng Shao*

^aShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China Email: shaoxusheng@ecust.edu.cn Email: lizhong@ecust.edu.cn
Xiaoyong Xu

^aShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China Email: shaoxusheng@ecust.edu.cn Email: lizhong@ecust.edu.cn
Zhong Li*

^aShanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, P. R. of China Email: shaoxusheng@ecust.edu.cn Email: lizhong@ecust.edu.cn

^bShanghai Collaborative Innovation Center for Biomanufacturing Technology, 130 Meilong Road, Shanghai 200237, P. R. of China

Abstract

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Abstract

Two practical and efficient approaches have been developed to synthesize two kinds of racemic spiroisobenzofuranopyrrole analogues as regioisomers. In the presence of sodium periodate, cis-indeno[1,2-b]pyrrol-4(1H)-ones were converted into spiro[isobenzofuran-1,2′-pyrrole] derivatives by a two-step process. In addition, oxidative reactions promoted by lead tetraacetate were demonstrated using cis-indeno[2,1-b]pyrrol-8(1H)-ones as substrates, affording spiro[isobenzofuran-1,3′-pyrrole] derivatives. The remarkable features of two approaches included mild and convenient reaction conditions, a broad substrate scope, and moderate to excellent yields. Possible mechanisms were proposed based on the comparison of the intermediates and products.

Key words

oxidation - regioisomer - cis-indeno[1,2-b]pyrrol-4(1H)-one - spiro[isobenzofuran-1,2′-pyrrole] - cis-indeno[2,1-b]pyrrol-8(1H)-one - spiro[isobenzofuran-1,3′-pyrrole]

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References

References and Notes
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14 For the preparation of starting materials, see the Supporting Information. All chiral compounds in this manuscript were obtained as racemic mixtures.
15 Crystallographic data have been deposited with the accession number CCDC 1029163 in the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk; website: www.ccdc.cam.ac.uk/conts/retrieving.html.
16 CCDC 1029164.
17 Typical Procedure for 2-{-[(6-Chloropyridin-3-yl)methyl]-5-hydroxy-7-nitro-6-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazol-5-yl}benzoic acid (3a) The suspension of 1-[(6-chloropyridin-3-yl)methyl]-4a,9a-dihydroxy-10-nitro-2,3,4a,9a-tetrahydroindeno[2′,1′:4,5]pyrrolo[1,2-a]imidazol-9(1H)-one (1a, 414 mg, 1 mmol) and NaIO₄ (214 mg, 1 mmol) in H₂O (10 mL) was stirred at r.t. for 4 h. The resulting solid 3a was isolated by filtration, washed with H₂O and dried; light yellow solid; yield 395 mg (92%); mp 151–152 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 13.11 (br s, 1 H), 8.47 (d, J = 2.4 Hz, 1 H), 7.88 (dd, J ₁ = 8.4 Hz, J ₂ = 2.4 Hz, 1 H), 7.78 (d, J = 7.6 Hz, 1 H), 7.60 (d, J = 8.4 Hz, 1 H), 7.57–7.51 (m, 1 H), 7.49–7.41 (m, 2 H), 5.36 (d, J = 16.0 Hz, 1 H), 5.10 (d, J = 16.0 Hz, 1 H), 4.04 (td, J ₁ = 10.8 Hz, J ₂ = 3.6 Hz, 1 H), 3.90 (q, J = 10.8 Hz, 1 H), 3.54 (q, J = 10.8 Hz, 1 H), 3.27 (td, J ₁ = 9.6 Hz, J ₂ = 4.0 Hz, 1 H) ppm. ¹³C NMR (100 MHz, DMSO-d ₆): δ =185.7, 170.2, 164.4, 149.6, 148.9, 139.0, 133.4, 133.2, 131.4, 129.6, 128.8, 128.7, 127.3, 124.3, 110.9, 85.6, 52.9, 48.5, 39.4 ppm. ESI-HRMS: m/z calcd for C₁₉H₁₆N₄O₆ ³⁵Cl [M + H]⁺: 431.0758; found: 431.0755; m/z calcd for C₁₉H₁₆N₄O₆ ³⁷Cl [M + H]⁺: 433.0729; found: 433.0747
18 Typical Procedure for 1′-[(6-Chloropyridin-3-yl)methyl]-7′-nitro-2′,3′-dihydro-3H-spiro{isobenzofuran-1,5′-pyrrolo[1,2-a]imidazole}-3,6′(1′H)-dione (4a) The mixture of PTSA·H₂O (19.1 mg, 0.1 mmol) and 2-{1-[(6-chloropyridin-3-yl)methyl]-5-hydroxy-7-nitro-6-oxo-2,3,5,6-tetrahydro-1H-pyrrolo[1,2-a]imidazol-5-yl}benzoic acid (3a, 430 mg, 1 mmol) in MeOH (10 mL) was heated to 60 °C and stirred for 4 h. Product 4a precipitated and was separated from the mixture by filtration; light yellow solid; yield 358 mg (87%); mp 317–318 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 8.55 (d, J = 2.4 Hz, 1 H), 8.04 (d, J = 8.0 Hz), 8.01 (dd, J ₁ = 8.4 Hz, J ₂ = 2.4 Hz), 7.92 (t, J = 7.2 Hz, 1 H), 7.87 (d, J = 7.6 Hz, 1 H), 7.81 (t, J = 7.6 Hz, 1 H), 7.61 (d, J = 8.0 Hz, 1 H), 5.35 (d, J = 16.0 Hz, 1 H), 5.20 (d, J = 16.0 Hz, 1 H), 4.18–4.03 (m, 2 H), 3.67–3.57 (m, 1 H), 3.39–3.31 (m, 1 H) ppm. ¹³C NMR (100 MHz, DMSO-d ₆): δ = 180.1, 167.4, 164.6, 150.3, 149.9, 140.7, 139.9, 135.9, 132.5, 131.2, 127.3, 126.2, 124.8, 124.1, 111.4, 92.2, 54.4, 49.6, 40.6 ppm. ESI-HRMS: m/z calcd for C₁₉H₁₄N₄O₅ ³⁵Cl [M + H]⁺: 413.0653; found: 413.0641; m/z calcd for C₁₉H₁₄N₄O₅ ³⁷Cl [M + H]⁺: 415.0623; found: 415.0641
19 Typical Procedure for 3′,3′-Dimethyl-8′-nitro-1′,2′,3′,4′-tetrahydro-3H,7′H-spiro{isobenzofuran-1,6′-pyrrolo[1,2-a]pyri-midine}-3,7′-dione (4j) The suspension of 5a,10a-dihydroxy-3,3-dimethyl-11-nitro-1,2,3,4,5a,10a-hexahydro-10H-indeno[2′,1′:4,5]pyrrolo[1,2-a]-pyrimidin-10-one (1j, 331 mg, 1 mmol) and NaIO₄ (214 mg, 1 mmol) in H₂O (10 mL) was stirred at r.t. for 4 h. The mixture was filtered, and the precipitated product 4j was washed with H₂O and dried; white solid; yield 253 mg (77%); mp 165–166 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 9.94 (s, 1 H), 8.02 (d, J = 7.6 Hz, 1 H), 7.93–7.97 (m, 1 H), 7.86–7.77 (m, 2 H), 3.25 (q, J = 12.4 Hz, 2 H), 2.96 (d, J = 11.7 Hz, 1 H), 2.65 (d, J = 11.7 Hz, 1 H), 0.99 (s, 3 H), 0.98 (s, 3 H) ppm. ¹³C NMR (100 MHz, DMSO-d ₆): δ = 175.4, 167.1, 157.9, 141.2, 135.6, 132.0, 126.9, 125.5, 123.5, 109.4, 93.5, 49.7, 47.6, 27.0, 23.4, 23.2 ppm. ESI-HRMS: m/z calcd for C₁₆H₁₆N₃O₅ [M + H]⁺: 330.1090; found: 330.1093
20 Typical Procedure for 1′-[(6-Chloropyridin-3-yl)methyl]-7′-nitro-2′,3′-dihydro-1′,3H,5′-spiro{isobenzofuran-1,6′-pyrrolo[1,2-a]imidazole}-3,5′-dione (5a) The mixture of 1-[(6-chloropyridin-3-yl)methyl)-4a,9b-dihydroxy-10-nitro-2,3,4a,9b-tetrahydroindeno[1′,2′:4,5]pyrrolo[1,2-a]imidazol-5(1H)-one (2a, 414 mg, 1 mmol) and Pb(OAc)₄ (488 mg, 1.1 mmol) in AcOH (5 mL) was stirred at r.t. for 3 h. The precipitate was separated from the mixture by filtration and washed with AcOH (2 mL) and EtOH (4 mL) to afford the pure product 5a; white solid; yield 387 mg (94%); mp 263–264 °C. ¹H NMR (400 MHz, DMSO-d ₆): δ = 8.55 (s, 1 H), 7.97 (t, J = 7.2 Hz, 2 H), 7.87–7.83 (m, 2 H), 7.71–7.68 (m, 1 H), 7.63 (d, J = 8.0 Hz, 1 H), 5.48–5.37 (m, 2 H), 4.21 (t, J = 8.0 Hz, 2 H), 3.91 (t, J = 8.8 Hz, 2 H) ppm. ¹³C NMR (100 MHz, DMSO-d ₆): δ = 169.1, 164.3, 155.2, 150.4, 149.8, 145.5, 139.9, 135.4, 131.2, 131.0, 126.6, 125.5, 124.8, 122.8, 100.7, 89.5, 56.8, 49.2, 39.0 ppm. ESI-HRMS: m/z calcd for C₁₉H₁₃N₄O₅ ³⁵ClK [M + K]⁺: 451.0212; found: 451.0198; m/z calcd for C₁₉H₁₃N₄O₅ ³⁷ClK [M + K]⁺: 453.0182; found: 453.0174

Supplementary Material

Supporting Information (PDF)