A Facile Synthesis of Telisatin A via Microwave-Promoted Annulation and ­Reformatsky Reaction

Nopporn Thasana; Ben Bjerke-Kroll; Somsak Ruchirawat

doi:10.1055/s-2008-1042764

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Synlett 2008(4): 505-508
DOI: 10.1055/s-2008-1042764

LETTER

A Facile Synthesis of Telisatin A via Microwave-Promoted Annulation and Reformatsky Reaction

Nopporn Thasana*^a,b, Ben Bjerke-Kroll^b, Somsak Ruchirawat*^a-c
^a Chulabhorn Graduate Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand
Fax: +66(2)5742027; e-Mail: nopporn@cri.or.th;
^b Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Vipavadee Rangsit Highway, Bangkok 10210, Thailand
^c Programme on Research and Development of Synthetic Drugs, Institute of Science and Technology for Research and Development, Mahidol University, Salaya Campus, Nakhonpathom 73170, Thailand

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Publication History

Received 15 August 2007
Publication Date:
12 February 2008 (online)

Abstract
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Abstract

A facile one-pot synthesis of 2,3-dioxopyrrolo[2,1-a]isoquinolines is reported involving the ring formation of aryl pyruvate derivatives with 3,4-dihydroisoquinolines under basic conditions and utilizing the Reformatsky reaction. Using microwave irradiation, the required compounds were obtained in moderate to good yields.

Key words

microwave - annulation - Reformatsky reaction - dioxopyrrolo[2,1-a]isoquinoline - dioxoaporphine

References and Notes

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14

Synthesis of 2,3-Dioxopyrrolo[2,1- a ]isoquinoline 2; Typical Procedure (Conditions C): A mixture of imines 4 (0.1 mmol), aryl pyruvates 5 (0.1 mmol) and NaOMe (0.1 mmol) in DMF (1 mL) was irradiated using microwave. The microwave run time was set to 2 min, with power at 300 W, temperature at 150 °C, and pressure at 100 psi, and the conditions were maintained for 10 min. The reaction was quenched with H₂O and extracted with EtOAc, dried (Na₂SO₄) and evaporated in vacuo to yield a red residue. The residue was purified by column chromatography, affording crystals of 2 after recrystallization in moderate yields (54-78%).
Conditions D: A mixture of imines 4 (0.1 mmol), aryl pyruvates 5 (0.1 mmol), copper powder (0.1 mmol) and zinc powder (0.1 mmol) in DMF (1 mL) was irradiated using microwave. The microwave run time was set to 2 min, with power at 300 W, temperature at 150 °C, and pressure at 100 psi, and the conditions were maintained for 10 min. The reaction was quenched with H₂O and extracted with EtOAc, dried (Na₂SO₄) and evaporated in vacuo to yield a red residue. The residue was purified by column chromatog
raphy, affording crystals of 2 after recrystallization in moderate to good yields (60-82%). Compound 2a: deep-red solid; mp 178-179 °C (EtOAc-hexane). IR (CHCl₃): 3020, 1745, 1701, 1580, 1492, 1290 cm^-1. ¹H NMR (200 MHz, CDCl₃): δ = 3.09 (t, J = 6.2 Hz, 2 H), 3.33 (s, 3 H), 3.85 (t, J = 6.2 Hz, 2 H), 3.96 (s, 3 H), 6.77 (s, 1 H), 6.95 (s, 1 H), 7.37 (m, 5 H). ¹³C NMR (50 MHz, CDCl₃): δ = 28.6, 36.6, 55.3, 56.2, 111.2, 112.2, 116.8, 127.9, 128.9, 130.2, 130.3, 132.8, 147.9, 153.5, 157.4, 158.3, 165.9, 183.1. MS (EI): m/z (%) = 263 (7), 306 (100), 307 (26), 335 (58) [M⁺]. HRMS (FAB): m/z [M + H⁺] calcd for C₂₀H₁₇NO₄: 336.1236; found: 336.1234.
Compound 2b: wine-red solid; mp 198-199 °C (EtOAc-hexane; lit [8c] 176-178 °C). IR (KBr): 1746, 1692, 1575, 1514, 1396, 1290, 1223 cm^-1. ¹H NMR (200 MHz, CDCl₃): δ = 3.11 (t, J = 6.2 Hz, 2 H), 3.30 (s, 3 H), 3.89 (t, J = 6.2 Hz, 2 H), 3.95 (s, 3 H), 6.65 (s, 1 H), 6.78 (s, 1 H), 7.31 (m, 3 H), 7.71 (d, J = 7.2 Hz, 1 H). ¹³C NMR (50 MHz, CDCl₃): δ = 28.4, 36.4, 55.2, 56.2, 107.9, 111.2, 111.5, 116.9, 125.9, 128.0, 129.9, 132.5, 132.8, 133.2, 148.3, 153.8, 158.1, 158.4, 181.6. MS (EI): m/z (%) = 306 (83), 334 (100), 384 (34), 386 (31), 413 (31) [M⁺], 415 (31) [M⁺ + 2]. HRMS (FAB): m/z [M + H⁺] calcd for C₂₀H₁₆BrNO₄: 414.0341; found: 414.0343.
Compound 2c: deep-red solid; mp 178-179 °C (EtOAc-hexane). IR (CHCl₃): 2941, 1742, 1692, 1573, 1472, 1403, 1343, 1299, 1111, 1029 cm^-1. ¹H NMR (200 MHz, CDCl₃): δ = 3.10 (t, J = 6.2 Hz, 2 H), 3.30 (s, 3 H), 3.81 (t, J = 6.2 Hz, 2 H), 3.89 (s, 3 H), 3.95 (s, 3 H), 6.82 (s, 1 H), 7.34 (m, 3 H), 7.37 (m, 2 H). ¹³C NMR (100 MHz, CDCl₃): δ = 21.7, 36.1, 55.2, 61.0, 61.1, 109.1, 119.3, 125.6, 128.0, 128.9, 130.1, 130.2, 147.1, 147.7, 150.5, 151.9, 157.1, 157.9, 183.4. MS (EI): m/z (%) = 237 (37), 336 (100), 365 (60) [M⁺]. HRMS (FAB): m/z [M + H⁺] calcd for C₂₁H₁₉NO₅: 366.1341; found: 366.1338.
Compound 2d: wine-red solid; mp 153-155 °C (EtOAc-hexane). IR (KBr): 1747, 1703, 1576, 1467, 1425, 1397, 1341, 1109, 1024 cm^-1. ¹H NMR (200 MHz, CDCl₃): δ = 3.11 (t, J = 6.6 Hz, 2 H), 3.20 (s, 3 H), 3.75 (t, J = 6.2 Hz, 2 H), 3.81 (s, 3 H), 3.87 (s, 3 H), 6.46 (s, 1 H), 7.20 (m, 2 H), 7.33 (t, J = 7.0 Hz, 1 H), 7.64 (d, J = 7.2 Hz, 1 H). ¹³C NMR (50 MHz, CDCl₃): δ = 21.7, 36.2, 55.2, 61.0, 61.1, 108.6, 119.4, 125.4, 125.8, 128.0, 129.9, 132.3, 132.7, 133.2, 147.0, 150.6, 152.3, 157.9, 158.0, 182.0. MS (EI): m/z (%) = 336 (54), 364 (100), 414 (34), 416 (36), 443 (93) [M⁺], 445 (95) [M⁺ + 2]. HRMS (FAB): m/z [M + H⁺] calcd for C₂₁H₁₈BrNO₅: 444.0447; found: 444.0449.