17 5 2005 9 PROGRESS IN CHEMISTRY Vol. 17 No. 5 Sep. 2005 3 FTIR 3 3 ( 650091) : O657. 3 ; O621. 3 : A : 10052281X(2005) 0520889208 Applications of FTIR in Solid2Phase Organic Synthesis Huang Qiang Long Quan Zheng Baozhong 3 3 (Department of Materials Science and Engineering Yunnan University Kunming 650091 China) Abstract Recent Progress in the applications of transmission diffuse reflectance attenuated total reflection photoacoustic and microscopic Fourier2transform infrared spectroscopy for qualitative and quantitative analyses in solid2 phase organic synthesis is reviewed. Key words combinatorial chemistry ; solid2phase organic synthesis ; FTIR [1 (SPOS) 3 ] (MAS2NMR) [12 13 ] [4 7 ] [8 ] [14 ; (SPIMS) 16 ] [9 ] SPOS [10 ] SPOS SPOS MAS2 (TLC) ( HPLC) NMR SPIMS (cleave (FTIR) and analyze) [11 ] [17 ] SPOS IR : ; : 2004 9 : 2005 1 3 (No. 20172044) (No. 2000YP04) 3 3 e2mail : bzhzheng @ynu. edu. cn
890 17 ; SPOS FTIR SPOS FTIR SPOS Yan [18 ] : SPOS FTIR TLC 3 : ( transmission ) ( reflectance ) (photoacoustic ) (micro2ftir) SPOS FTIR FTIR FTIR Scheme 1 KBr IR Sarhan [20 ] IR Merrifield 7 42 8 ( scheme 2) 5mg KBr Merrifield 7 42 8 32 FTIR SPOS ( PS2DVB Merifield Wang C O (1 695cm - 1 ) ) (1 595cm - 1 ) ( PS2PEGTentaGel ) C O C IR ( < 2m) (1 150cm - 1 ) PS2PEG FTIR (1 595cm - 1 ) [17 ] Gordeev [19 ] KBr FTIR 9 m n 1 42 (1 42dihydropyridine DHP) 6 (scheme 1) 3 FTIR 1 735cm - 1 1 715cm - 1 6 1 705cm - 1 DHP 4 3 Scheme 2 13 C2NMR Gordeev KBr FT2IR FTIR
5 FTIR 891 : (1) KBr Arsequell [24 ] ; (2) (S H) (2 555cm - 1 ) ; (3) KBr ; (4) FTIR 1. FTIR DRIETS Goswami [25 ] DRIETS ; O 3 Si (CH 2 β 3 (spacer) 12 1 82 (DHAQ) 13 14 ( scheme 4) 14 C O C N (1 630cm - 1 ) (1 595 1 535 1 500 1 460 1 415 FTIR 1 345cm - 1 ) FTIR (DRIFTS) SPOS : (1) ; (2) [21 3mg Deben ] 015 1mg ; (3) ; (4) ; (5) SPOS PS PS2PEG 100 400 30 Scheme 3 Scheme 4 150m IR 2m 2. (attenuated total reflectance ATR) 2m KBr (internal reflection) IR [22 ] Sofia [23 ; DRIFTS (2 108cm - 1 ) TentaGel 10 11 IR ART2FTIR (scheme 3) DRIFTS KBr (30 s) ART2FTIR : (1)
892 17 SynPhase TM ; (2) IR ; (3) IR ; (4) FTIR ART2FTIR SPOS [17 18 ] Karavoltsos [26 ] Micro2FTIR 15 N C 16 (DIPEA) 17 ( scheme 5) ART2FTIR (1 814cm - 1 ) ATR (1 712cm - 1 ) 1. Scheme 5 ATR2FTIR SPOS IR Gears Crowns Lanterns ( single2bead [27 28 ] FTIR) Yan [32 ] : Mimotopes SynPhase TM [29 30 ] Merrifield Gears Crowns Lanterns SynPhase TM SynPhase TM IR SynPhase TM Yan [31 ] 18 20 (scheme 6) 3 450cm - 1 1 800cm - 1 1 740cm - 1 2 120cm - 1 1 800cm - 1 1 670cm - 1 ART2FTIR Scheme 6
5 FTIR 893 Gly2Gly2Gly 24 2 IR Fmoc d 9 2Boc 25 Merrifield Wang Rink (Fmoc2Lys2(Boc2d 9 )2OH) (C D) ( 2 TentaGel 300 2 200cm - 1 ) IR Merrifield [33 ] S N 2 TentaGel Wang Yan [34 ] Wang 21 2 ( site2site interaction) (scheme 7) 2 10 Wang (1 795cm - 1 ) (1 728cm - 1 ) 22 23 2 23 ; 10 22 Wang [18 36 37 ] SPOS 2 20 2 SPOS (spacer) SPOS IR Scheme 7 (scheme 8) Scheme 8 IR SPOS Yan [38 ] 3 SPOS SPOS IR 2. ATR Huber [39 ] ATR SPOS ATR Yan (314mmolg - 1 ) Merrifield Russell 7 (scheme 9) [35 ] KBr 27 ( C N )
894 17 KBr ATR 100m ATR Scheme 9 Gosselin [40 ] (1 645cm - 1 ) (N H + ) (3 200 cm - 1 ) 36 25 (scheme 10) 33 (1 741cm - 1 1 718cm - 1 ) p2 34 (1 674cm - 1 ) 28 IR (2 231cm - 1 ) (N H) (3 413 cm - 1 ) ; 31 32 (1 678cm - 1 ) ( C S C) (1 250cm - 1 ) ( O S O ) (1 325cm - 1 1 125cm - 1 ) ATR (1 429cm - 1 ) (1 741cm - 1 1 718cm - 1 ) 40 5 % Huber ( ATR ) ( 100m) IR Scheme 10 Michelson ( PA2FTIR) DRITTS ATR PA2FTIR IR PA2FTIR
5 FTIR 895 ( m2cpba) 34 [ 3 ] 35 ( O S O ) (1 140cm - 1 ) ; 1 82 [51410 ] 272(DBU) 35 36 ( O S O ) (1 140cm - 1 ) ATR PA2FTIR PA2FTIR Basso [41 ] PA2FTIR Lantern2HMPA(42hydroxymethylphenoxyacetic acid) 37 N2Fmoc ( N2Fmoc2Phe) Passerini ( scheme 11) (2 150cm - 1 ) (1 705cm - 1 ) (1 670cm - 1 ) Scheme 11 FTIR TLC 536 FTIR [ 1 ] James I W. Tetrahedron 1999 55 : 4855 4946 [ 2 ] (Xu J X). (Chin. J. Org. Chem. ) 1998 18 : 1 10 (Li W Z) ( Yun L H). (Chin. J. Org. Chem. ) 1998 18 : 403 413 [ 4 ] Thompson L A Ellman J A. Chem. Rev. 1996 96 : 555 600 [ 5 ] Dewitt D H Czarnik A W. Acc. Chem. Res. 1996 29 : 114 122 [ 6 ] Franzen R G. J. Comb. Chem. 2000 2 : 195 214 [ 7 ] Dolle R E. J. Comb. Chem. 2002 4 : 369 418 [ 8 ] Petsko G A. Nature 1996 384 : 7 14 [ 9 ] ( Xu J ). ( Progress in Chemistry) 1999 11 : 286 299 [10] (Xu J X) (Ma Y). ( Chemistry) 2002 (3) : 145 152 [11] Kay C Lorthioir O E Parr N J et al. Biotechnol. Bioeng. (Comb. Chem. ) 2000Π2001 71 : 110 118 [12] Keifer P A. J. Org. Chem. 1996 61 : 1558 1559 [13] Ferngndez2Forner D Huerta J M Ferrer M et al. Tetrahedron Lett. 2002 43 : 3543 3546 [14] Egner B J Langley GJ Bradley M. J. Org. Chem. 1995 60 : 2652 2653 [15] Egner B J Bradle M. Tetrahedron 1997 53 : 14021 14030 [16] Roice M Kumar K S Pillai V N R. Tetrahedron 2000 56 : 3725 3734 [17] Dal Cin M Marchioro C Passarini M et al. IL Farmaco 2002 57 : 497 510 [18] Yan B Gremlich H U. J. Chromatography B 1999 725 : 91 102 [19] Gordeev M F Patel D V Gordon E M. J. Org. Chem. 1996 61 : 924 928 [20] Sarhan A A Abdelaal M Y Ali M M et al. Polymer 1998 40 : 233 241 [21] Deben I Goorden J van Doornum E et al. Eur. J. Org. Chem. 1998 697 700 [22] (Wu Q) ( Yang S Z) (Luo J T). (Spectroscopy and Spectral Analysis) 2000 20 : 606 609 [23] Chan T Y Chen R Sofia M J et al. Tetrahedron Lett. 1997 38 : 2821 2824 [24] Arsequell G Gonzglez A Valencia G. Tetrahedron Lett. 2001 42 : 2685 2687 [25] Goswami A Singh A K. Talanta 2002 58 : 669 678 [26] Karavoltsos M Mourtas S Gatos D et al. Tetrahedron Lett. 2003 44 : 3979 3982 [27] Gremlich H U Berets S L. Appl. Spectrosc. 1996 50 : 532 [28] Bedos P Feliu L Martinez J. Tetrahedron Lett. 2003 44 : 4937 4939 [29] Rasoul F Ercole F Pham Y et al. Biopolym. 2000 55 : 207 216 [30] Ede N J. J. Immunol. Meth. 2002 267 : 3 11 [31] Yan B Kumaravel G Anjaria H et al. J. Org. Chem. 1995 60 : 5736 5738 [32] Yan B Kumaravel G. Tetrahedron 1995 51 : 843 848
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