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Synlett

Volumn , Issue 2, 2008, Pages 263-267

Synthesis of a calothrixin B isomer with a novel 7H-indolo[2,3-j] phenanthridine-7,13(8H)-dione structure

(6) Maingot, Lucie a Thuaud, Frédéric a Sissouma, Drissa a,b Collet, Sylvain a Guingant, André a Evain, Michel c

a Centre National de la Recherche Scientifique (France)

b UNIVERSITÉ FÉLIX HOUPHOUËT BOIGNY (Côte d’Ivoire)

c INSTITUT DES MATÉRIAUX JEAN ROUXEL (France)

Author keywords

2 bromo 1H carbazole 1,4(9H) dione; 7H indolo 2,3 j phenanthridine 7,13(8H) dione; Calothrixin B isomer; Hetero Diels Alder reaction

Indexed keywords

3,4 DIHDYRO 2H INDOLO[2,3 J] PHENANTHRIDINE 1,7,13 (8H) TRIONE; 8H INDOLO[2,3 J]PHENANTHRIDINE 7,13 DIONE; CALOTHRIXIN B; INDOLE DERIVATIVE; PHENANTHRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIELS ALDER REACTION; ISOMER; POLARIZATION; SYNTHESIS;

EID: 38849111839 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000933 Document Type: Article

Times cited : (15)

References (25)

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16
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- Benzyl 2-Bromo-1,4-dioxo-1H-carbazole-9(4 H)-carboxylate (6b, orange solid; mp 148°C. 1H NMR (300 MHz, CDCl3, δ, 5.53 (s, 2 H, OCH2Ph, 7.23 (s, 1 H, H-3, 7.30-7.70 (m, 7 H, HAr, 7.99 (d, J, 8.4 Hz, 1 H, H-8, 8.28 (d, J, 7.5 Hz, 1 H, H-5, 13C NMR (75 MHz, CDCl3, δ, 71.0 (OCH2Ph, 114.5 (C-3, 122.8 (quaternary C, 123.2 (quaternary C, 123.4 (CHAr, 126.1 (CH Ar, 128.8 (2 x CHAr, 129.2 (3 x CHAr, 129.7 (CHAr, 133.6 (quaternary C, 133.8 (quaternary C, 137.6 (quaternary C, CHAr, 138.8 (quaternary C, 149.9 (NCO, 170.2 (C-1, 181.2 (C-4, FT-IR (KBr, 3300, 3054, 1755, 1682, 1654 cm-1. MS (Cl, NH3, m/z, 427 [M, NH4, 79Br, 410 [M, H, 79Br, 366, 332, 145, 91. HRMS EI
- 4: 408.9950; found: 408.9954.

17
- 38849086872
- C20H12BrNO4: The data set was collected on a Nonius-Bruker Kappa CCD diffractometer, using the Mo-KL2,3 radiation. C20H12BrNO4 (M, 410.2, triclinic, space group P1, Dc, 1.660 g cm-3, a, 7.1218(3, b, 9.6798(4, c, 13.2182(7) Å, α, 72.048(3)°, β, 84.294(6)°, γ, 71.184(5)°, V, 820.54(7) Å3, Z, 2, λ, 0.71069 Å, μ, 2.532 mm-1, T, 150 K, R(F2, 0.0547 for 3460 observed reflections [I > 2 σ(I, and RWF2, 0.1183 for all 4692 reflections. The data have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 654172
- 2) = 0.1183 for all 4692 reflections. The data have been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 654172.

18
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- The orientation of addition of 6b to 5 is governed by the bromo substituent. We have already observed such an effect in previous works.12 First observations were reported by Cameron et al. 13
- 13

19
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20
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21
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22
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- 4-Dihydro-2H-indolo[2,3-j] phenanthridine-1,7,13 (8H)-trione (22, To a stirred solution of diene 5 (250 mg, 1.47 mmol) in anhydrous CHCl3 (5 mL) at r.t was added a solution of dienophile 6b (400 mg, 0.98 mmol) in anhydrous CHCl3 (8 mL, After the mixture was heated at 50°C for 18 h, it was cooled to r.t. and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with EtOAc-hexanes, 1:1) to give the cycloadduct 22 (215 mg, 0.68 mmol, 70, as an orange-red solid: mp >300°C (CHCl3-hexanes, dec, 1H NMR (300 MHz, DMSO, δ, 2.20 (quint, J, 6.3 Hz, 2 H, H-3, 2.91 (t, J, 6.6 Hz, 2 H, H-2, 3.12 (t, J, 6.0 Hz, 2 H, H-4, 7.42 (t, J, 7.5 Hz, 1 H, H-10 or H-11, 7.52 (t, J, 7.5 Hz, 1 H, H-11 or H-10, 7.65 (d, J, 8.4 Hz, 1 H, H-9, 8.12 d, J, 7.8 Hz, 1 H, H-12
- 2g display distinguishable NMR signals (Δδ = 0.06 ppm).

23
- 38849098586
- 2NH·HBr generated in the course of the Diels-Alder primary adduct aromatization process.
- 2NH·HBr generated in the course of the Diels-Alder primary adduct aromatization process.

24
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- Cacchi, S.¹ Ciattini, P.G.² Morera, E.³ Ortar, G.⁴

25
- 38849091539
- 8H-Indolo[2,3-j]phenanthridine-7, 13-dione (2, red solid; mp >350°C 1H NMR (300 MHz, DMSO, δ, 7.35 (t, J, 7.2 Hz, 1 H, HAr, 7.43 (t, J, 7.2 Hz, 1 H, HAr, 7.56 (d, J, 8.4 Hz, 1 H, HAr, 7.81 (t, J, 7.6 Hz, 1 H, HAr, 7.91 (t, J, 7.6 Hz, 1 H, HAr, 8.10 (d, J, 8.4 Hz, 1 H, HAr, 8.20 (d, J, 8.0 Hz, 1 H, HAr, 9.50 (s, 1 H, H-6, 9.65 (d, J, 8.4 Hz, 1 H, HAr, 13.10 (br s, 1 H, NH, 13C NMR (75 MHz, DMSO, δ, 114.0 (CHAr, 118.5 (quaternary C, 122.3 (CHAr, 123.0 (quaternary C, 124.0 (2 x quaternary C, 124.3 (CHAr, 127.1 (CHAr, 127.9 (CHAr, 129.7 (CHAr, 129.9 (CHAr, 131.8 (CHAr, 134.1 (quaternary C, 135.4 (quaternary C, 138.4 (quaternary C, 146.9 CH A
- 2: 298.0742; found: 298.0743.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.