C-N Bond-Linked Conjugates of Dibenz[b,f][1,4]oxazepines with 2-Oxindole

Xinglong Xing; Jinlong Wu; Jialu Luo; Wei-Min Dai

doi:10.1055/s-2006-948172

LETTER

C-N Bond-Linked Conjugates of Dibenz[b,f][1,4]oxazepines with 2-Oxindole

Xinglong Xing^a, Jinlong Wu^a, Jialu Luo^a, Wei-Min Dai*^a,b
^a Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Fax: +86(571)87953128; e-Mail: chdai@zju.edu.cn;
^b Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, P. R. of China
Fax: +85223581594; e-Mail: chdai@ust.hk;

Abstract

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Abstract

An expeditious synthesis of highly functionalized dibenz[b,f][1,4]oxazepin-11(10H)-ones and dibenz[b,f][1,4]-oxazepine-11(10H)-carboxamides has been established via microwave-assisted one-pot U-4CR and intramolecular O-arylation. A Pd-catalyzed intramolecular amidation was successfully performed under microwave irradiation to furnish the novel conjugates of dibenz[b,f][1,4]oxazepin-11(10H)-ones with a 2-oxindole linked through a C-N single bond.

Key words

U-4CR - microwaves - heterocycles - palladium - lactams

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References

References and Notes

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Selected Spectroscopic Data.
Compound 3c: a white crystalline solid; mp 234-235 °C (EtOAc-hexane). IR (KBr): 3422, 2929, 1647, 1344 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 8.73 (d, J = 2.4 Hz, 1 H), 8.22 (dd, J = 8.4, 2.8 Hz, 1 H), 7.57 (d, J = 7.6 Hz, 1 H), 7.43 (d, J = 8.0 Hz, 1 H), 7.39 (d, J = 7.6 Hz, 1 H), 7.24 (d, J = 8.8 Hz, 1 H), 7.19 (t, J = 7.6 Hz, 1 H), 7.05 (t, J = 7.6 Hz, 1 H), 6.89 (s, 1 H), 6.72 (d, J = 8.0 Hz, 1 H), 6.13 (s, 1 H), 6.01 (br s, 1 H), 3.94-3.86 (m, 1 H), 2.14 (s, 3 H), 2.02-1.93 (m, 2 H), 1.71-1.55 (m, 3 H), 1.40-1.30 (m, 2 H), 1.23-1.12 (m, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 167.8, 165.6, 165.4, 154.4, 145.1, 138.3, 133.7, 133.6, 132.2, 130.5, 129.2, 128.7, 127.5, 127.5, 126.8 (br), 126.1, 121.7, 121.6, 68.3 (br and very weak), 49.4, 33.1, 33.1, 31.2 (for minor atropisomer), 25.8, 25.1, 25.0, 20.9 (two carbons are missing due to atropisomerism). MS (+ESI): m/z (%) = 586 (100) [M + Na⁺]. Anal. Calcd for C₂₈H₂₆BrN₃O₅: C, 59.58; H, 4.64; N, 7.44. Found: C, 59.32; H, 4.63; N, 7.56.
Compound 4a: a white crystalline solid; mp 171-174 °C (EtOAc-hexane); R _f = 0.25 (17% EtOAc in hexane). IR (KBr): 3280, 2929, 1654, 1522, 1345, 1266 cm^-1. ¹H NMR (400 MHz, CDCl₃): δ = 8.18 (dd, J = 8.8, 2.4 Hz, 1 H), 8.11 (d, J = 2.8 Hz, 1 H), 7.47 (d, J = 7.6 Hz, 2 H), 7.40 (d, J = 8.8 Hz, 1 H), 7.36 (t, J = 7.6 Hz, 1 H), 7.27-7.23 (m, 2 H), 7.16 (d, J = 8.4 Hz, 1 H), 6.98 (d, J = 8.0 Hz, 1 H), 6.76 (s, 1 H), 6.40 (s, 1 H), 6.28 (br d, J = 8.0 Hz, 1 H), 3.70-3.60 (m, 1 H), 1.94 (s, 3 H), 1.88-1.84 (m, 1 H), 1.80-1.50 (m, 4 H), 1.40-1.08 (m, 5 H). ¹³C NMR (100 MHz, CDCl₃): δ = 171.3, 166.3, 158.8, 148.9, 142.7, 135.3, 133.4, 131.5, 131.4, 130.1 (x2), 129.9 (x2), 128.9, 128.2, 127.5, 124.6, 123.8, 122.1, 121.2, 61.3, 48.4, 33.2, 32.7, 25.3, 24.6, 20.4. MS (+ESI): m/z (%) = 508 (100) [M + Na⁺], 486 (14) [M + H⁺]. Anal. Calcd for C₂₈H₂₇N₃O₅: C, 69.26; H, 5.61; N, 8.65. Found: C, 69.28; H, 5.65; N, 8.65.
Compound 5c: a white crystalline solid; mp 222-224 °C. IR (KBr): 3448, 2924, 1654, 1348 cm^-1. ¹H NMR (500 MHz, DMSO-d ₆, 80 °C): δ = 8.42 (br s, 1 H), 8.37 (dd, J = 9.0, 3.0 Hz, 1 H), 7.59 (d, J = 9.0 Hz, 1 H), 7.30-7.26 (m, 4 H), 7.18 (d, J = 8.0 Hz, 1 H), 7.08 (br s, 1 H), 6.99 (t, J = 8.0 Hz, 1 H), 5.90-5.60 (br s, 1 H), 4.14-4.08 (m, 1 H), 2.31 (s, 3 H), 2.29-2.09 (m, 2 H), 1.89-1.70 (m, 5 H), 1.46-1.24 (m, 3 H). ¹³C NMR (125 MHz, DMSO-d ₆, 80 °C): δ = 172.0, 164.3, 162.8 (br and weak), 152.5, 144.8, 143.2, 137.8, 131.4 (br and weak), 128.9, 128.7, 127.5, 127.5, 126.2, 125.5, 123.5 (br), 123.1 (br), 122.0, 121.8, 121.7, 109.8, 62.8 (br and weak), 52.6, 28.7, 28.4, 25.6, 25.0, 20.1. MS (+ESI): m/z 506 (100) [M + Na⁺]. Anal. Calcd for C₂₈H₂₅N₃O₅: C, 69.55; H, 5.21; N, 8.69. Found: C, 69.55; H, 5.23; N, 8.69.