Studies on New Strategies for the Synthesis of Oligomeric 1,2,3-Triazoles

Yong-Ming Wu; Juan Deng; Qing-Yun Chen

doi:10.1055/s-2006-933098

LETTER

Studies on New Strategies for the Synthesis of Oligomeric 1,2,3-Triazoles

Yong-Ming Wu*, Juan Deng, Qing-Yun Chen*
Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Rd., Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: ymwu@mail.sioc.ac.cn;

Abstract

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Abstract

Conjugated tetra-1,2,3-triazoles were synthesized by the coupling reaction of terminal alkynes.

Key words

5-iodo-1,2,3-triazole - iodo-1,3-diploar cycloaddition reaction - conjugated tetra-1,2,3-triazoles - Sonogashira reaction

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References

References and Notes

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3′-Benzyl-5-iodo-3′ H -[1,4′]-bis-1,2,3-triazolyl-4,5′-dicarboxylic Acid Dimethyl Ester(4a). Yield 97%; white solid; mp 136-137 °C. ¹H NMR (CDCl₃): δ = 3.85 (s, 3 H), 4.02 (s, 3 H), 5.27-5.84 (m, 2 H), 6.92-6.98 (m, 2 H), 7.20-7.31 (m, 3 H). IR: 732, 1071, 1252, 1612, 1726, 1738, 3002 cm^-1. MS: m/z (%) = 440 (1) [M - 28]⁺, 341 (4), 254 (30), 216 (20), 142 (26), 91 (100), 65 (6). Anal. Calcd for C₁₅H₁₃IN₆O₄: C, 38.48; H, 2.80; N, 17.95. Found: C, 38.61; H, 2.68; N, 18.19.
5-Iodo-3′-(2,2,3,3-tetrafluoropropyl)-3′ H -[1,4′]-bis-1,2,3-triazolyl-4,5′-dicarboxylic Acid Dimethyl Ester (4b). Yield 75%; white solid; mp 117-118 °C. ¹H NMR (CDCl₃): δ = 3.91 (s, 3 H), 4.05 (s, 3 H), 4.85-4.95 (m, 1 H), 5.05-5.15 (m, 1 H), 5.88 (tt, J ₁ = 2 Hz, J ₂ = 53 Hz, 1 H). ¹⁹F NMR (CDCl₃): δ = -135.32 (dd, J ₁ = 53 Hz, J ₂ = 53 Hz, 2 F),
-118.95 (td, J ₁ = 14 Hz, J ₂ = 39 Hz, 2 F). MS: m/z (%) = 365 (2) [M - 127]⁺, 240 (100), 182 (58), 168 (22), 51 (43), 42 (36). IR: 996, 1227, 1523, 1616, 1734, 2967, 3006 cm^-1. Anal. Calcd for C₁₁H₉F₄IN₆O₄: C, 26.85; H, 1.84; N, 17.08. Found: C, 26.84; H, 1.90; N, 16.95.

The crystal data of 7d has been deposited at the Cambridge Crystallographic Data Centre and allocated; the deposition number is CCDC 294495. Crystal system, space group: triclinic, P-1. Unit cell dimensions: a = 9.6157 (14) Å, b = 13.262 (2) Å, c = 14.903 (2) Å, α = 66.689 (2)°, β = 75.647 (3)°, γ = 80.962 (3)°; volume: 1687.2 (4) A³; Z, calcd density: 4, 1.937 mg/m³; absorption coefficient: 1.972 mm^-1; F(000): 952; crystal size: 0.232 × 0.135 × 0.092 mm; theta range for data collection: 1.52-25.50°; completeness to θ = 25.50, 97.5%; data/restraints/parameters: 6121/3/474; goodness-of-fit on F ²: 1.089; final R indices [I > 2σ(1)]: R1 = 0.0831, wR2 = 0.2804; R indices (all data): R1 = 0.1018, wR2 = 0.2921; largest diff. peak and hole: 2.191 and -0.919 e A^-3

Compound 11: yield 78%; yellow solid; mp 190-191 °C. ¹H NMR (CDCl₃): δ = 5.67 (s, 4 H), 7.36-7.50 (m, 16 H), 8.07-8.13 (m, 4 H). IR: 700, 739, 774, 911, 1345, 1455, 3030 cm^-1. MS: m/z (%) = 517 (7) [M⁺], 311 (39), 221 (33), 170 (100), 91 (10), 77 (27), 57 (55). Anal. Calcd for C₃₄H₂₄N₆: C, 79.05; H, 4.68; N, 16.27. Found: C, 78.79; H, 4.63; N, 16.30.

Compound 12: yield 81%; white solid; mp 206-207 °C. ¹H NMR (CDCl₃): δ = 5.45 (s, 4 H), 5.70 (s, 4 H), 6.96-7.11 (m, 20 H), 7.31-8.43 (m, 10 H). ¹³C NMR (CDCl₃): δ = 53.03, 53.54, 68.54, 85.29, 119.51, 122.35, 127.08, 127.69, 127.73, 128.20, 128.51, 128.59, 129.07, 130.43, 133.59, 134.52, 139.91, 147.43. IR: 696, 726, 1227, 1456, 1496, 3032 cm^-1. MS (MALDI): m/z = 1.9 [M + 1]⁺. HRMS: m/z calcd for C₅₂H₃₈N₁₂: 830.3357; found: 830.3337.

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