POCl 3-mediated H-bonding-directed one-pot synthesis of macrocyclic pentamers, strained hexamers and highly strained heptamers

Science China Chemistry

Volumn 55, Issue 1, 2012, Pages 55-63

  Liu, Ying ^a   Qin, Bo ^b   Zeng, Huaqiang ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b CHONGQING UNIVERSITY   (China)

Author keywords

foldamer; H bond; macrocycles; one pot synthesis; POCl 3; supramolecular chemistry

Indexed keywords

FOLDAMER; H-BOND; MACROCYCLES; ONE-POT SYNTHESIS; POCL 3;

CHLORINE COMPOUNDS; FUNCTIONAL GROUPS; KINETICS; ORGANIC POLYMERS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL);

DIMERS;

EID: 84856315272     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-011-4438-0     Document Type: Article

References (91)

1. Pedersen CJ. Cyclic polyethers and their complexes with metal salts. J Am Chem Soc, 1967, 89: 7017-7086
2. Dietrich B, Lehn JM, Sauvage J-P. Diazapolyoxamacrocycles and macrobicycles. Tetrahedron Lett, 1969, 34: 2885-2889
3. Kyba EP, Siegel MG, Sousa LR, Sogah GDY, Cram DJ. Chiral, hinged, and functionalized multiheteromacrocycles. J Am Chem Soc, 1973, 95: 2691-2692
4. Sanford AR, Yuan L, Feng W, Yamato K, Flowersb RA, Gong B. Cyclic aromatic oligoamides as highly selective receptors for the guanidinium ion. Chem Commun, 2005: 4720-4722 (Pubitemid 41475765)
5. Shirude PS, Gillies ER, Ladame S, Godde F, Shin-Ya K, Huc I, Balasubramanian S. Macrocyclic and helical oligoamides as a new class of g-quadruplex ligands. J Am Chem Soc, 2007, 129: 11890-11891 (Pubitemid 47512006)
6. Helsel AJ, Brown AL, Yamato K, Feng W, Yuan LH, Clements AJ, Harding SV, Szabo G, Shao ZF, Gong B. Highly conducting transmembrane pores formed by aromatic oligoamide macrocycles. J Am Chem Soc, 2008, 130: 15784-15785
7. Zhu YY, Li C, Li GY, Jiang XK, Li ZT. Hydrogen-bonded aryl amide macrocycles: Synthesis, single-crystal structures, and stacking interactions with fullerenes and coronene. J Org Chem, 2008, 73: 1745-1751 (Pubitemid 351438889)
8. Qin B, Chen XY, Fang X, Shu YY, Yip YK, Yan Y, Pan SY, Ong WQ, Ren CL, Su HB, et al. Crystallographic evidence of an unusual, pentagon-shaped folding pattern in a circular aromatic pentamer. Org Lett, 2008, 10: 5127-5130
9. Qin B, Ren CL, Ye RJ, Sun C, Chiad K, Chen XY, Li Z, Xue F, Su HB, Chass GA, et al. Persistently folded circular aromatic amide pentamers containing modularly tunable cation-binding cavities with high ion selectivity. J Am Chem Soc, 2010, 132: 9564-9566
10. Qin B, Ong WQ, Ye RJ, Du ZY, Chen XY, Yan Y, Zhang K, Su HB, Zeng HQ. Highly selective one-pot synthesis of H-bonded pentagon-shaped circular aromatic pentamers. Chem Commun, 2011, 47: 5419-5421
11. Knops P, Sendhoff N, Mekelburger HB, Voegtle F. High dilution reactions - New synthetic applications. Top Curr Chem, 1992, 161: 1-36
12. Faust R. Explosions as a synthetic tool? Cycloalkynes as precursors to fullererenes, buckytubes and buckyonions. Angew Chem Int Ed, 1998, 37: 2825-2828 (Pubitemid 29008563)
13. Höger S. Shape-persistent macrocycles: From molecules to materials. Chem Eur J, 2004, 10: 1320-1329
14. Zhang W, Moore JS. Shape-persistent macrocycles: Structures and synthetic approaches from arylene and ethynylene building blocks. Angew Chem Int Ed, 2006, 45: 4416-4439 (Pubitemid 44109600)
15. Woodward RB, Au-Yeung BW, Balaram P, Browne LJ, Ward DE, Au-Yeung BW, Balaram P, Browne LJ, Card PJ, Chen CH. Asymmetric total synthesis of erythromycin. 2. Synthesis of an erythronolide A lactone system. J Am Chem Soc, 1981, 103: 3213-3215 (Pubitemid 11038206)
16. Eschenmoser A. Vitamin B12: Experiments concerning the origin of its molecular structure. Angew Chem Int Ed, 1988, 27: 5-39 (Pubitemid 18043269)
17. Xing LY, Ziener U, Sutherland TC, Cuccia LA. Hydrogen bond directed synthesis of pyridazine and naphthyridine containing macrocycles. Chem Commun, 2005: 5751-5753 (Pubitemid 43028745)
18. Imabeppu F, Katagiri K, Masu H, Kato T, Tominaga M, Therrien B, Takayanagi H, Kaji E, Yamaguchi K, Kagechika H, et al. Calix[3]amides-bowlshaped cyclic trimers toward building block for molecular recognition: Self-complementary dimeric structure in the crystal. Tetrahedron Lett, 2006, 47: 413-416 (Pubitemid 41797363)
19. Campbell F, Plante J, Carruthers C, Hardie MJ, Prior TJ, Wilson AJ. Macrocyclic scaffolds derived from p-aminobenzoic acid. Chem Commun, 2007: 2240-2242 (Pubitemid 46848681)
20. Yokoyama A, Maruyama T, Tagami K, Masu H, Katagiri K, Azumaya I, Yokozawa T. One-pot synthesis of cyclic triamides with a triangular cavity from trans-stilbene and diphenylacetylene monomers. Org Lett, 2008, 10: 3207-3210
21. Katagiri K, Tohaya T, Masu H, Tominaga M, Azumaya I. Effect of aromatic-aromatic interactions on the conformational stabilities of macrocycle and preorganized structure during macrocyclization. J Org Chem, 2009, 74: 2804-2810
22. Campbell F, Wilson AJ. An 'impossible' macrocyclisation using conformation directing protecting groups. Tetrahedron Lett, 2009, 50: 2236-2238
23. He L, An Y, Yuan L, Yamato K, Feng W, Gerlitz O, Zheng C, Gong B. Macrocyclic aromatic tetrasulfonamides with a stable cone conformation. Chem Commun, 2005: 3788-3790 (Pubitemid 41139741)
24. He L, An Y, Yuan LH, Feng W, Li MF, Zhang DC, Yamato K, Zheng C, Zeng XC, Gong B. Shape-persistent macrocyclic aromatic tetrasulfonamides: Molecules with nanosized cavities and their nanotubular assemblies in solid state. Proc Natl Acad Sci USA, 2006, 103: 10850-10855 (Pubitemid 44148384)
25. Geng M, Zhang D, Wu X, He L, Gong B. One-pot formation and characterization of macrocyclic aromatic tetrasulfonates. Org Lett, 2009, 11: 923-926
26. Carver FJ, Hunter CA, Shannon RJ. Directed macrocyclization reactions. Chem Commun, 1994: 1277-1280
27. Yuan L, Feng W, Yamato K, Sanford AR, Xu D, Guo H, Gong B. Highly efficient, one-step macrocyclizations assisted by the folding and preorganization of precursor oligomers. J Am Chem Soc, 2004, 126:11120-11121 (Pubitemid 39223163)
28. Zhang AM, Han YH, Yamato K, Zeng XC, Gong B. Aromatic oligoureas: Enforced folding and assisted cyclization. Org Lett, 2006, 8: 803-806 (Pubitemid 43411969)
29. Ahn HC, Yun SM, Choi K. A proline-based macrocyclic amide with S-4 symmetry. Chem Lett, 2008, 37: 10-11
30. Feng W, Yamato K, Yang LQ, Ferguson JS, Zhong LJ, Zou SL, Yuan LH, Zeng XC, Gong B. Efficient kinetic macrocyclization. J Am Chem Soc, 2009, 131: 2629-2637
31. Jiang H, Leger JM, Guionneau P, Huc I. Strained aromatic oligoamide macrocycles as new molecular clips. Org Lett, 2004, 6: 2985-2988 (Pubitemid 39178056)
32. Hui JKH, MacLachlan MJ. [6+6] Schiff-base macrocycles with 12 imines: Giant analogues of cyclohexane. Chem Commun, 2006: 2480-2482 (Pubitemid 43877082)
33. Ferguson JS, Yamato K, Liu R, He L, Zeng XC, Gong B. One-pot formation of large macrocycles with modifiable peripheries and internal cavities. Angew Chem Int Ed, 2009, 48: 3150-3154
34. Filarowski A, Koll A, Sobczyk L. Intramolecular hydrogen bonding in o-hydroxy Aryl Schiff Bases. Curr Org Chem, 2009, 13: 172-193
35. Li F, Gan Q, Xue L, Wang ZM, Jiang H. H-bonding directed one-step synthesis of novel macrocyclic peptides from ε-aminoquinolinecarboxylic acid. Tetrahedron Lett, 2009, 50: 2367-2369
36. Yang LQ, Zhong LJ, Yamato K, Zhang XH, Feng W, Deng PC, Yuan LH, Zeng XC, Gong B. Aromatic oligoamide macrocycles from the bimolecular coupling of folded oligomeric precursors. New J Chem, 2009, 33: 729-733
37. Zoua S, Hea Y, Yanga Y, Zhaoa Y, Yuana L, Feng W, Yamato K, Gong B. Improving the efficiency of forming 'unfavorable' products: eight-residue macrocycles from folded aromatic oligoamide precursors. Synlett. 2009, 9
38. Hu JC, Feng W, Li XH, Yang LQ, Yuan LH, He L, Gong B. One-pot formation of aromatic oligoamide macrocycles and the corresponding mechanism. Acta Phys Chim Sin, 2010, 26: 1811-1822
39. Yang YA, Yuan LH, Hu JC, Zou SL, Feng W, Gong B. Spherical assemblies of cyclo[6]aramide with polar side chains. Acta Phys Chim Sin, 2010, 26: 1557-1564
40. Qin B, Sun C, Liu Y, Shen J, Ye RJ, Zhu J, Duan XF, Zeng HQ. One-pot synthesis of hybrid macrocyclic pentamers with variable functionalizations around the periphery. Org Lett, 2011, 13: 2270-2273
41. Qin B, Shen S, Sun C, Du ZY, Zhang K, Zeng HQ. One-pot multi-molecular macrocyclization for the expedient synthesis of macrocyclic aromatic pentamers by a chain growth mechanism. Chem Asian J, 2011: asia.201100409
42. For some recent reviews in foldamers, see: (a) Gellman SH. Foldamers: A manifesto. Acc Chem Res, 1998, 31: 173-180 (Pubitemid 128474551)
43. Gong B. Crescent oligoamides: From acyclic "macrocycles" to folding nanotubes. Chem Eur J, 2001, 7: 4336-4342 (Pubitemid 33000550)
44. Hill DJ, Mio MJ, Prince RB, Hughes TS, Moore JS. A field guide to foldamers. Chem Rev, 2001, 101: 3893-4011 (Pubitemid 35373050)
45. Sanford AR, Gong B. Evolution of helical foldamers. Curr Org Chem, 2003, 7: 1649-1659 (Pubitemid 37254301)
46. Sanford AR, Yamato K, Yang X, Yuan L, Han Y, Gong B. Well-defined secondary structures - Information-storing molecular duplexes and helical foldamers based on unnatural peptide backbones. Eur J Biochem, 2004, 271: 1416-1425 (Pubitemid 38553548)
47. Huc I. Aromatic oligoamide foldamers. Eur J Org Chem, 2004: 17-29
48. Cheng RP. Beyond de novo protein design-de novo design of non-natural folded oligomers. Curr Opin Struc Biol, 2004, 14: 512-520 (Pubitemid 39094357)
49. Li ZT, Hou JL, Li C, Yi HP. Shape-persistent aromatic amide oligomers: New tools for supramolecular chemistry. Chem Asian J, 2006, 1: 766-778
50. Gong B. Hollow crescents, helices, and macrocycles from enforced folding and folding-assisted macrocyclization. Acc Chem Res, 2008, 41: 1376-1386
51. Li ZT, Hou JL, Li C. Peptide mimics by linear arylamides: A structural and functional diversity test. Acc Chem Res, 2008, 41: 1343-1353
52. Horne WS, Gellman SH. Foldamers with heterogeneous backbones. Acc Chem Res, 2008, 41: 1399-1408
53. Haldar D, Schmuck C. Metal-free double helices from abiotic backbones. Chem Soc Rev, 2009, 38: 363-371
54. Hamuro Y, Geib SJ, Hamilton AD. Novel molecular scaffolds: Formation of helical secondary structure in a family of oligoanthranilamides. Angew Chem Int Ed, 1994, 33: 446-448 (Pubitemid 24987374)
55. Hamuro Y, Geib SJ, Hamilton AD. Oligoanthranilamides. non-peptide subunits that show formation of specific secondary structure. J Am Chem Soc, 1996, 118: 7529-7541 (Pubitemid 26279807)
56. Hamuro Y, Geib SJ, Hamilton AD. Novel folding patterns in a family of oligoanthranilamides: Non-peptide oligomers that form extended helical secondary structures. J Am Chem Soc, 1997, 119: 10587-10593 (Pubitemid 27501277)
57. Berl V, Huc I, Khoury RG, Krische MJ, Lehn JM. Interconversion of single and double helices formed from synthetic molecular strands. Nature, 2000, 407: 720-723
58. Berl V, Huc I, Khoury R, Lehn JM. Helical molecular programming: supramolecular double helices by dimerization of helical oligopyridine- dicarboxamide strands. Chem Eur J, 2001, 7: 2810-2820 (Pubitemid 32641109)
59. Kolomiets E, Berl V, Odriozola I, Stadler AM, Kyritsakas N, Lehn JM. Contraction/extension molecular motion by protonation/deprotonation induced structural switching of pyridine derived oligoamides. Chem Commun, 2003: 2868-2869 (Pubitemid 37485411)
60. Zhu J, Parra RD, Zeng HQ, Skrzypczak-Jankun E, Zeng XC, Gong B. A new class of folding oligomers: Crescent oligoamides. J Am Chem Soc, 2000, 122: 4219-4220 (Pubitemid 30304860)
61. Gong B, Zeng HQ, Zhu J, Yuan LH, Han YH, Cheng SZ, Furukawa M, Parra RD, Kovalevsky AY, Mills JL, et al. Creating nanocavities of tunable sizes: Hollow helices. Proc Natl Acad Sci USA, 2002, 99: 11583-11588 (Pubitemid 34994442)
62. Yuan LH, Zeng HQ, Yamato K, Sanford AR, Feng W, Atreya HS, Sukumaran DK, Szyperski T, Gong B. Helical aromatic oligoamides: Reliable, readily predictable folding from the combination of rigidified structural motifs. J Am Chem Soc, 2004, 126: 16528-16537 (Pubitemid 40081953)
63. Yang XW, Yuan LH, Yamamoto K, Brown AL, Feng W, Furukawa M, Zeng XC, Gong B. Backbone-rigidified oligo(m-phenylene ethynylenes). J Am Chem Soc, 2004, 126: 3148-3162 (Pubitemid 38380720)
64. Corbin PS, Zimmerman SC, Thiessen PA, Hawryluk NA, Murray TJ. Complexation-induced unfolding of heterocyclic ureas. Simple foldamers equilibrate with multiply hydrogen-bonded sheetlike structures. J Am Chem Soc, 2001, 123: 10475-10488 (Pubitemid 33015693)
65. Jiang H, Leger J-M, Huc I. Aromatic δ-peptides. J Am Chem Soc, 2003, 125: 3448-3449 (Pubitemid 36512416)
66. Dolain C, Leger JM, Delsuc N, Gornitzka H, Huc I. Probing helix propensity of monomers within a helical oligomer. Proc Natl Acad Sci USA, 2005, 102: 16146-16151 (Pubitemid 41688882)
67. Haldar D, Jiang H, Leger JM, Huc I. Interstrand interactions between side chains in a double-helical foldamer. Angew Chem Int Ed, 2006, 45: 5483-5486 (Pubitemid 44384331)
68. Gan Q, Bao CY, Kauffmann B, Grelard A, Xiang JF, Liu SH, Huc I, Jiang H. Quadruple and double helices of 8-fluoroquinoline oligoamides. Angew Chem Int Ed, 2008, 47: 1715-1718
69. Hou JL, Shao XB, Chen GJ, Zhou YX, Jiang XK, Li ZT. Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides. J Am Chem Soc, 2004, 126: 12386-12394 (Pubitemid 39304920)
70. Li C, Ren SF, Hou JL, Yi HP, Zhu SZ, Jiang XK, Li ZT. F⋯H-N Hydrogen bonding driven foldamers: Efficient receptors for dialkylammonium Ions. Angew Chem Int Ed, 2005, 44: 5725-5729 (Pubitemid 41312163)
71. Hou JL, Yi HP, Sha XB, Li C, Wu ZQ, Jian XK, Wu LZ, Tung CH, Li ZT. Helicity induction in hydrogen-bonding-driven zinc porphyrin foldamers by chiral C60-incorporating histidines. Angew Chem Int Ed, 2006, 45: 796-800 (Pubitemid 43151403)
72. Cai W, Wang GT, Xu YX, Jiang XK, Li ZT. Vesicles and organogels from foldamers: A solvent-modulated self-assembling process. J Am Chem Soc, 2008, 130: 6936-6937 (Pubitemid 351770129)
73. Rebek J. Molecular behavior in small spaces. Acc Chem Res, 2009, 42: 1660-1668
74. Kanamori D, Okamura TA, Yamamoto H, Ueyama N. Linear-to-turn conformational switching induced by deprotonation of unsymmetrically linked phenolic oligoamides. Angew Chem Int Ed, 2005, 44: 969-972 (Pubitemid 40239035)
75. Li X, Zhan CL, Wang YB, Yao JN. Pyridine-imide oligomers. Chem Commun, 2008: 2444-2446 (Pubitemid 351713218)
76. Yan Y, Qin B, Shu YY, Chen XY, Yip YK, Zhang DW, Su HB, Zeng HQ. Helical organization in foldable aromatic oligoamides by a continuous hydrogen-bonding network. Org Lett, 2009, 11: 1201-1204
77. Yan Y, Qin B, Ren CL, Chen XY, Yip YK, Ye RJ, Zhang DW, Su HB, Zeng HQ. Synthesis, structural investigations, hydrogen-deuterium exchange studies, and molecular modeling of conformationally stablilized aromatic oligoamides. J Am Chem Soc, 2010, 132: 5869-5879
78. Ong WQ, Zhao HQ, Du ZY, Yeh JZY, Ren CL, Tan LZW, Zhang K, Zeng HQ. Computational prediction and experimental verification of pyridine-based helical oligoamides containing four repeating units per turn. Chem Commun, 2011, 47: 6416-6418
79. Ong WQ, Zhao HQ, Fang X, Woen S, Zhou F, Yap WL, Su HB, Li SFY, Zeng HQ. Encapsulation of conventional and unconventional water dimers by water-ninding foldamers. Org Lett, 2011, 13: 3194-3197
80. Ren CL, Xu SY, Xu J, Chen HY, Zeng HQ. Planar macrocyclic fluoropentamers as supramolecular organogelators. Org Lett, 2011: 3840-3843
81. Ren CL, Maurizot V, Zhao HQ, Shen J, Zhou F, Ong WQ, Du ZY, Zhang K, Su HB, Zeng HQ. Fivefold-symmetric macrocyclic aromatic pentamers: High affinity cation recognition, ion-pair induced columnar stacking and nanofibrillation. J Am Chem Soc, 2011, 133: 13930-13933
82. Ren CL, Zhou F, Qin B, Ye RJ, Shen S, Su HB, Zeng HQ. Crystallographic realization of the mathematically predicted densest "All Pentamer" packing lattice by C5-symmetric "sticky" fluoropentamers. Angew Chem Int Ed, 2011: DOI: 10.1002/anie.201101553
83. Zhang Z, Xia B, Han C, Yu Y, Huang F. Syntheses of copillar[5]arenes by co-oligomerization of different monomers. Org Lett, 2010, 12: 3285-3287
84. Zhang Z, Luo Y, Xia B, Han C, Yu Y, Chen X, Huang F. Four constitutional isomers of BMpillar[5]arene: Synthesis, crystal structures and complexation with n-octyltrimethyl ammonium hexafluorophosphatew. Chem Commun, 2011, 47: 2417-2419
85. Guieu S, Crane AK, MacLachlan MJ. Campestarenes: Novel shape-persistent Schiff base macrocycles with 5-fold symmetry. Chem Commun, 2011, 47: 1169-1171
86. Du ZY, Ren CL, Ye RJ, Shen J, Lu YJ, Wang J, Zeng HQ. BOP-mediated one-pot synthesis of C5-symmetric macrocyclic pyridone pentamers. Chem Commun, 2011, 47: 12488-12490
87. Frisch MJ: In Gaussian 03, Gaussian, Inc. Edited by: Wallingford CT; 2004
88. Becke AD. Density functional thermochemistry. III. The role of exact exchange. J Chem Phys, 1993, 98: 5648-5652
89. Petersson GA, Bennett A, Tensfeldt TG, Al-Laham MA, Shirley WA, Mantzaris J. A complete basis set model chemistry. I. The total energies of closed shell atoms and hydrides of the first row elements. J Chem Phys, 1988, 89: 2193-2218
90. Petersson GA, Al-Laham MA. A complete basis set model chemistry. II. Open shell systems and the total energies of the first row atoms. J Chem Phys, 1991, 94: 6081-6090
91. Carried out by using mechanism-based kinetics simulator avaiable from http://www.stolaf.edu/depts/chemistry/courses/toolkits/126/js/kinetics/index.htm