144
4 Applications of Nitrile Imine Derivatives
19. Donohue SR, Halldin C, Pike VW (2008) A facile and regioselective synthesis of Rimonabant
through an Enamine-directed 1,3-dipolar cycloaddition. Tetrahedron Lett 49:2789–2791
20. Oh LM (2006) Synthesis of celecoxib via 1,3-dipolar cycloaddition. Tetrahedron Lett
47:7943–7946
21. Oh LM, Wang H, Shilcrat SC, Herrmann RE, Patience DB, Spoors PG, Sisko J (2007) Development of a scalable synthesis of GSK183390A, a PPAR α/γ Agonist. Org Process Res Dev
11:1032–1042
22. Tamborini L, Chen Y, Foss CA, Pinto A, Horti AG, Traynelis SF, De Micheli C, Mease RC,
Hansen KB, Conti P, Pomper MG (2016) Development of radiolabeled ligands targeting the
glutamate binding site of the N-Methyl-d-aspartate receptor as potential imaging agents for
brain. J Med Chem 59:11110–11119
23. Tóth M, Kun S, Bokor É, Benltifa M, Tallec G, Vidal S, Docsa T, Gergely P, Somsák L,
Praly J-P (2009) Synthesis and structure-activity relationships of C-glycosylated oxadiazoles
as inhibitors of glycogen phosphorylase. Bioorg Med Chem 17:4773–4785
24. Donohue AC, Pallich S, McCarthy TD (2001) Cycloaddition of nitrile imines to resin-bound
Enamines: a solid phase synthesis of 1,4-Diarylpyrazoles. J Chem Soc Perkin Trans 1:2817–
2822
25. Manyem S, Sibi MP, Lushington GH, Neuenswander B, Schoenen F, Aubé J (2006) Solutionphase parallel synthesis of a library of 2-Pyrazolines. J Comb Chem 9:20–28
26. Garanti L, Molteni G, Casati P (2002) Nitrilimine cycloadditions to MeOPEG-bounded
alkenyl dipolarophiles. J Chem Soc Perkin Trans 1:2504–2508
27. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a
few good reactions. Angew Chemie Int Ed 40:2004–2021
28. Lim RKV, Lin Q (2010) Bioorthogonal chemistry: recent progress and future directions. Chem
Commun 46:1589
29. Lim RKV, Lin Q (2011) Photoinducible bioorthogonal chemistry: a spatiotemporally
controllable tool to visualize and perturb proteins in live cells. Acc Chem Res 44:828–839
30. Ramil CP, Lin Q (2014) Photoclick chemistry: a fluorogenic light-triggered in vivo ligation
reaction. Curr Opin Chem Biol 21:89–95
31. Herner A, Lin Q (2016) Photo-triggered click chemistry for biological applications. Top Curr
Chem 374:1
32. Song W, Wang Y, Qu J, Lin Q (2008) Selective functionalization of a genetically encoded
alkene-containing protein via “Photoclick Chemistry” in bacterial cells. J Am Chem Soc
130:9654–9655
33. Csongár C, Weinberg P, Slezak H, Tomaschewski G (1988) Photochemistry of Arylsubstituted
2H-Tetrazoles X. Sulfonated 2,5-Diaryl-2H-tetrazoles. J für Prakt Chemie 330:629–633
34. Molteni G, Orlandi M, Broggini G (2000) Nitrilimine cycloadditions in aqueous media. J
Chem Soc Perkin Trans 1:3742–3745
35. Song W, Wang Y, Qu J, Madden MM, Lin Q (2008) A Photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins. Angew Chemie
Int Ed 47:2832–2835
36. Wang Y, Song W, Hu WJ, Lin Q (2009) Fast alkene functionalization in vivo by photoclick
chemistry: HOMO lifting of Nitrile Imine dipoles. Angew Chem Int Ed Engl 48:5330–5333
37. Wang J, Zhang W, Song W, Wang Y, Yu Z, Li J, Wu M, Wang L, Zang J, Lin Q (2010) A
biosynthetic route to photoclick chemistry on proteins. J Am Chem Soc 132:14812–14818
38. Lee Y-J, Wu B, Raymond JE, Zeng Y, Fang X, Wooley KL, Liu WR (2013) A genetically
encoded acrylamide functionality. ACS Chem Biol 8:1664–1670
39. Yu Z, Lin Q (2014) Design of Spiro[2.3]hex-1-ene, a genetically encodable double-strained
alkene for superfast photoclick chemistry. J Am Chem Soc 136:4153–4156
40. Song W, Wang Y, Yu Z, Vera CIR, Qu J, Lin Q (2010) A metabolic alkene reporter for
spatiotemporally controlled imaging of newly synthesized proteins in mammalian cells. ACS
Chem Biol 5:875–885
41. Kaya E, Vrabel M, Deiml C, Prill S, Fluxa VS, Carell T (2012) A genetically encoded
Norbornene amino acid for the mild and selective modification of proteins in a copper-free
click reaction. Angew Chemie Int Ed 51:4466–4469
4 Applications of Nitrile Imine Derivatives
19. Donohue SR, Halldin C, Pike VW (2008) A facile and regioselective synthesis of Rimonabant
through an Enamine-directed 1,3-dipolar cycloaddition. Tetrahedron Lett 49:2789–2791
20. Oh LM (2006) Synthesis of celecoxib via 1,3-dipolar cycloaddition. Tetrahedron Lett
47:7943–7946
21. Oh LM, Wang H, Shilcrat SC, Herrmann RE, Patience DB, Spoors PG, Sisko J (2007) Development of a scalable synthesis of GSK183390A, a PPAR α/γ Agonist. Org Process Res Dev
11:1032–1042
22. Tamborini L, Chen Y, Foss CA, Pinto A, Horti AG, Traynelis SF, De Micheli C, Mease RC,
Hansen KB, Conti P, Pomper MG (2016) Development of radiolabeled ligands targeting the
glutamate binding site of the N-Methyl-d-aspartate receptor as potential imaging agents for
brain. J Med Chem 59:11110–11119
23. Tóth M, Kun S, Bokor É, Benltifa M, Tallec G, Vidal S, Docsa T, Gergely P, Somsák L,
Praly J-P (2009) Synthesis and structure-activity relationships of C-glycosylated oxadiazoles
as inhibitors of glycogen phosphorylase. Bioorg Med Chem 17:4773–4785
24. Donohue AC, Pallich S, McCarthy TD (2001) Cycloaddition of nitrile imines to resin-bound
Enamines: a solid phase synthesis of 1,4-Diarylpyrazoles. J Chem Soc Perkin Trans 1:2817–
2822
25. Manyem S, Sibi MP, Lushington GH, Neuenswander B, Schoenen F, Aubé J (2006) Solutionphase parallel synthesis of a library of 2-Pyrazolines. J Comb Chem 9:20–28
26. Garanti L, Molteni G, Casati P (2002) Nitrilimine cycloadditions to MeOPEG-bounded
alkenyl dipolarophiles. J Chem Soc Perkin Trans 1:2504–2508
27. Kolb HC, Finn MG, Sharpless KB (2001) Click chemistry: diverse chemical function from a
few good reactions. Angew Chemie Int Ed 40:2004–2021
28. Lim RKV, Lin Q (2010) Bioorthogonal chemistry: recent progress and future directions. Chem
Commun 46:1589
29. Lim RKV, Lin Q (2011) Photoinducible bioorthogonal chemistry: a spatiotemporally
controllable tool to visualize and perturb proteins in live cells. Acc Chem Res 44:828–839
30. Ramil CP, Lin Q (2014) Photoclick chemistry: a fluorogenic light-triggered in vivo ligation
reaction. Curr Opin Chem Biol 21:89–95
31. Herner A, Lin Q (2016) Photo-triggered click chemistry for biological applications. Top Curr
Chem 374:1
32. Song W, Wang Y, Qu J, Lin Q (2008) Selective functionalization of a genetically encoded
alkene-containing protein via “Photoclick Chemistry” in bacterial cells. J Am Chem Soc
130:9654–9655
33. Csongár C, Weinberg P, Slezak H, Tomaschewski G (1988) Photochemistry of Arylsubstituted
2H-Tetrazoles X. Sulfonated 2,5-Diaryl-2H-tetrazoles. J für Prakt Chemie 330:629–633
34. Molteni G, Orlandi M, Broggini G (2000) Nitrilimine cycloadditions in aqueous media. J
Chem Soc Perkin Trans 1:3742–3745
35. Song W, Wang Y, Qu J, Madden MM, Lin Q (2008) A Photoinducible 1,3-dipolar cycloaddition reaction for rapid, selective modification of tetrazole-containing proteins. Angew Chemie
Int Ed 47:2832–2835
36. Wang Y, Song W, Hu WJ, Lin Q (2009) Fast alkene functionalization in vivo by photoclick
chemistry: HOMO lifting of Nitrile Imine dipoles. Angew Chem Int Ed Engl 48:5330–5333
37. Wang J, Zhang W, Song W, Wang Y, Yu Z, Li J, Wu M, Wang L, Zang J, Lin Q (2010) A
biosynthetic route to photoclick chemistry on proteins. J Am Chem Soc 132:14812–14818
38. Lee Y-J, Wu B, Raymond JE, Zeng Y, Fang X, Wooley KL, Liu WR (2013) A genetically
encoded acrylamide functionality. ACS Chem Biol 8:1664–1670
39. Yu Z, Lin Q (2014) Design of Spiro[2.3]hex-1-ene, a genetically encodable double-strained
alkene for superfast photoclick chemistry. J Am Chem Soc 136:4153–4156
40. Song W, Wang Y, Yu Z, Vera CIR, Qu J, Lin Q (2010) A metabolic alkene reporter for
spatiotemporally controlled imaging of newly synthesized proteins in mammalian cells. ACS
Chem Biol 5:875–885
41. Kaya E, Vrabel M, Deiml C, Prill S, Fluxa VS, Carell T (2012) A genetically encoded
Norbornene amino acid for the mild and selective modification of proteins in a copper-free
click reaction. Angew Chemie Int Ed 51:4466–4469