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Selective Synthesis of 2-, 4-, and 5-Cyano Substituted Imidazoles from Imidazole N-Oxides and Trimethylsilyl Cyanide.

The Journal of organic chemistry

Alcázar J, Begtrup M, de La Hoz A.
PMID: 11667594
J Org Chem. 1996 Oct 04;61(20):6971-6973. doi: 10.1021/jo960991s.

1-Substituted 2-, 4-, and 5-cyanoimidazoles were produced by reaction of 3-cyclohexyl or 3-p-tolylimidazole 1-oxide and trimethylsilyl cyanide in the presence of triethylamine. The product composition depended on reaction temperature and solvent polarity. By proper choice of these parameters each...

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Alcázar J, Begtrup M, de La Hoz A. Selective Synthesis of 2-, 4-, and 5-Cyano Substituted Imidazoles from Imidazole N-Oxides and Trimethylsilyl Cyanide. J Org Chem. 1996;61(20):6971-6973doi: 10.1021/jo960991s.
Alcázar, J., Begtrup, M., & de La Hoz, A. (1996). Selective Synthesis of 2-, 4-, and 5-Cyano Substituted Imidazoles from Imidazole N-Oxides and Trimethylsilyl Cyanide. The Journal of organic chemistry, 61(20), 6971-6973. https://doi.org/10.1021/jo960991s
Alcázar, Jesús, et al. "Selective Synthesis of 2-, 4-, and 5-Cyano Substituted Imidazoles from Imidazole N-Oxides and Trimethylsilyl Cyanide." The Journal of organic chemistry vol. 61,20 (1996): 6971-6973. doi: https://doi.org/10.1021/jo960991s
Alcázar J, Begtrup M, de La Hoz A. Selective Synthesis of 2-, 4-, and 5-Cyano Substituted Imidazoles from Imidazole N-Oxides and Trimethylsilyl Cyanide. J Org Chem. 1996 Oct 04;61(20):6971-6973. doi: 10.1021/jo960991s. PMID: 11667594.
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Efficient and beta-Stereoselective Synthesis of 4(5)-(beta-D-Ribofuranosyl)- and 4(5)-(2-Deoxyribofuranosyl)imidazoles(1).

The Journal of organic chemistry

Harusawa S, Murai Y, Moriyama H, Imazu T, Ohishi H, Yoneda R, Kurihara T.
PMID: 11667345
J Org Chem. 1996 Jun 26;61(13):4405-4411. doi: 10.1021/jo952136z.

A synthetic route to 4(5)-(beta-D-ribofuranosyl)imidazole (1), starting from 2,3,5-tri-O-benzyl-D-ribose (5), was developed via a Mitsunobu cyclization. Reaction of 5 with the lithium salt of bis-protected imidazole afforded the corresponding 5-ribosylimidazole 7RS. Hydrolysis of 7RS gave a 1:1 mixture of...

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Harusawa S, Murai Y, Moriyama H, et al. Efficient and beta-Stereoselective Synthesis of 4(5)-(beta-D-Ribofuranosyl)- and 4(5)-(2-Deoxyribofuranosyl)imidazoles(1). J Org Chem. 1996;61(13):4405-4411doi: 10.1021/jo952136z.
Harusawa, S., Murai, Y., Moriyama, H., Imazu, T., Ohishi, H., Yoneda, R., & Kurihara, T. (1996). Efficient and beta-Stereoselective Synthesis of 4(5)-(beta-D-Ribofuranosyl)- and 4(5)-(2-Deoxyribofuranosyl)imidazoles(1). The Journal of organic chemistry, 61(13), 4405-4411. https://doi.org/10.1021/jo952136z
Harusawa, Shinya, et al. "Efficient and beta-Stereoselective Synthesis of 4(5)-(beta-D-Ribofuranosyl)- and 4(5)-(2-Deoxyribofuranosyl)imidazoles(1)." The Journal of organic chemistry vol. 61,13 (1996): 4405-4411. doi: https://doi.org/10.1021/jo952136z
Harusawa S, Murai Y, Moriyama H, Imazu T, Ohishi H, Yoneda R, Kurihara T. Efficient and beta-Stereoselective Synthesis of 4(5)-(beta-D-Ribofuranosyl)- and 4(5)-(2-Deoxyribofuranosyl)imidazoles(1). J Org Chem. 1996 Jun 26;61(13):4405-4411. doi: 10.1021/jo952136z. PMID: 11667345.
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Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles.

The Journal of organic chemistry

Zaki ME, Proença MF, Booth BL.
PMID: 12530849
J Org Chem. 2003 Jan 24;68(2):276-82. doi: 10.1021/jo020347f.

1-Aryl-5-amino-4-(cyanoformimidoyl)imidazoles 2 were reacted with malononitrile under mild experimental conditions and led to 3-aryl-5,7-diamino-6-cyano-3H-imidazo[4,5-b]pyridines 5, when the reaction was carried out in the presence of DBU, or to 3-aryl-5-amino-6,7-dicyano-3H-imidazo[4,5-b]pyridines 3, in its absence. Both reactions evolved from the adduct...

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Zaki ME, Proença MF, Booth BL. Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles. J Org Chem. 2003;68(2):276-82doi: 10.1021/jo020347f.
Zaki, M. E., Proença, M. F., & Booth, B. L. (2003). Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles. The Journal of organic chemistry, 68(2), 276-82. https://doi.org/10.1021/jo020347f
Zaki, Magdi E A, et al. "Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles." The Journal of organic chemistry vol. 68,2 (2003): 276-82. doi: https://doi.org/10.1021/jo020347f
Zaki ME, Proença MF, Booth BL. Efficient synthesis of 3H-imidazo[4,5-b]pyridines from malononitrile and 5-amino-4-(cyanoformimidoyl)imidazoles. J Org Chem. 2003 Jan 24;68(2):276-82. doi: 10.1021/jo020347f. PMID: 12530849.
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Chemistry of Iron(III) in a Hemin-like Macrocyclic [N(4)](2)(-) Environment: Relationship between CT Absorption and EPR Spectra.

Inorganic chemistry

Jäger EG, Keutel H.
PMID: 11670031
Inorg Chem. 1997 Jul 30;36(16):3512-3519. doi: 10.1021/ic9702633.

The visible/near-IR and EPR spectra of the octahedral low-spin diadducts of the ethylene-bridged complex 6,13-diethoxycarbonyl-5,14-dimethyl-1,4,8,11-tetraazacyclotetradeca-4,6,12,14-tetraenato[2(-)]iron(III) iodide (1a-I), the ethylene/phenylene 1b-I, and the phenylene-bridged analogous complex 1c-I were investigated as a function of the axial and equatorial ligands. 1a-I forms...

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Jäger EG, Keutel H. Chemistry of Iron(III) in a Hemin-like Macrocyclic [N(4)](2)(-) Environment: Relationship between CT Absorption and EPR Spectra. Inorg Chem. 1997;36(16):3512-3519doi: 10.1021/ic9702633.
Jäger, E. G., & Keutel, H. (1997). Chemistry of Iron(III) in a Hemin-like Macrocyclic [N(4)](2)(-) Environment: Relationship between CT Absorption and EPR Spectra. Inorganic chemistry, 36(16), 3512-3519. https://doi.org/10.1021/ic9702633
Jäger, Ernst-G., and Keutel, Heike. "Chemistry of Iron(III) in a Hemin-like Macrocyclic [N(4)](2)(-) Environment: Relationship between CT Absorption and EPR Spectra." Inorganic chemistry vol. 36,16 (1997): 3512-3519. doi: https://doi.org/10.1021/ic9702633
Jäger EG, Keutel H. Chemistry of Iron(III) in a Hemin-like Macrocyclic [N(4)](2)(-) Environment: Relationship between CT Absorption and EPR Spectra. Inorg Chem. 1997 Jul 30;36(16):3512-3519. doi: 10.1021/ic9702633. PMID: 11670031.
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Design and Synthesis of New Biomimetic Materials by Sol-Gel: A Cu(II)(histidine)(2) Complex Covalently Bonded on a Silica Matrix.

Inorganic chemistry

Louloudi M, Deligiannakis Y, Hadjiliadis N.
PMID: 11670821
Inorg Chem. 1998 Dec 28;37(26):6847-6851. doi: 10.1021/ic980665q.

The synthesis of a new histidine-silane derivative, Boc-His(Boc)-CONH-(CH(2))(3)Si(OEt)(3), is reported. Hydrolysis and co-condensation of this monomer with tetraethoxysilane, via the sol-gel procedure, results in a hybrid inorganic-organic material that bears histidine molecules covalently bonded on a silica matrix. 1D-ESEEM...

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Louloudi M, Deligiannakis Y, Hadjiliadis N. Design and Synthesis of New Biomimetic Materials by Sol-Gel: A Cu(II)(histidine)(2) Complex Covalently Bonded on a Silica Matrix. Inorg Chem. 1998;37(26):6847-6851doi: 10.1021/ic980665q.
Louloudi, M., Deligiannakis, Y., & Hadjiliadis, N. (1998). Design and Synthesis of New Biomimetic Materials by Sol-Gel: A Cu(II)(histidine)(2) Complex Covalently Bonded on a Silica Matrix. Inorganic chemistry, 37(26), 6847-6851. https://doi.org/10.1021/ic980665q
Louloudi, Maria, et al. "Design and Synthesis of New Biomimetic Materials by Sol-Gel: A Cu(II)(histidine)(2) Complex Covalently Bonded on a Silica Matrix." Inorganic chemistry vol. 37,26 (1998): 6847-6851. doi: https://doi.org/10.1021/ic980665q
Louloudi M, Deligiannakis Y, Hadjiliadis N. Design and Synthesis of New Biomimetic Materials by Sol-Gel: A Cu(II)(histidine)(2) Complex Covalently Bonded on a Silica Matrix. Inorg Chem. 1998 Dec 28;37(26):6847-6851. doi: 10.1021/ic980665q. PMID: 11670821.
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Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-Z Mode: Convenient Route to 2-Aza-1,3-dienes.

The Journal of organic chemistry

Barroso MT, Kascheres A.
PMID: 11674083
J Org Chem. 1999 Jan 08;64(1):49-53. doi: 10.1021/jo980198u.

Reaction of 1-azirine-3-methylacrylates 1a,b with imidazoles and pyrazoles under mild conditions results in the formation of 2-aza-1,3-dienes 2a-g containing a potential leaving group at the 1-position. Simple alcohols (methanol and ethanol) react similarly with 1a,b in the presence of...

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Barroso MT, Kascheres A. Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-Z Mode: Convenient Route to 2-Aza-1,3-dienes. J Org Chem. 1999;64(1):49-53doi: 10.1021/jo980198u.
Barroso, M. T., & Kascheres, A. (1999). Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-Z Mode: Convenient Route to 2-Aza-1,3-dienes. The Journal of organic chemistry, 64(1), 49-53. https://doi.org/10.1021/jo980198u
Barroso, Marcia T., and Kascheres, Albert. "Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-Z Mode: Convenient Route to 2-Aza-1,3-dienes." The Journal of organic chemistry vol. 64,1 (1999): 49-53. doi: https://doi.org/10.1021/jo980198u
Barroso MT, Kascheres A. Electronically Mediated Selectivity in Ring Opening of 1-Azirines. The 3-Z Mode: Convenient Route to 2-Aza-1,3-dienes. J Org Chem. 1999 Jan 08;64(1):49-53. doi: 10.1021/jo980198u. PMID: 11674083.
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High Superoxide Dismutase Activity of a Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(II) Species. Design, Synthesis, Structure, and Magnetism of Copper(II) Complexes with a Mixed Pyrazole-Imidazole Donor Set.

Inorganic chemistry

Tabbì G, Driessen WL, Reedijk J, Bonomo RP, Veldman N, Spek AL.
PMID: 11669684
Inorg Chem. 1997 Mar 12;36(6):1168-1175. doi: 10.1021/ic961260d.

A new dinucleating ligand, 1,5-bis(1-pyrazolyl)-3-[bis(2-imidazolyl)methyl] azapentane (Hbpzbiap), containing pyrazoles and imidazoles has been designed and synthesized. The synthesis and characterization of the copper complexes with the ligand Hbpzbiap and its dehydronated form are described. This study is aimed at...

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Tabbì G, Driessen WL, Reedijk J, et al. High Superoxide Dismutase Activity of a Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(II) Species. Design, Synthesis, Structure, and Magnetism of Copper(II) Complexes with a Mixed Pyrazole-Imidazole Donor Set. Inorg Chem. 1997;36(6):1168-1175doi: 10.1021/ic961260d.
Tabbì, G., Driessen, W. L., Reedijk, J., Bonomo, R. P., Veldman, N., & Spek, A. L. (1997). High Superoxide Dismutase Activity of a Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(II) Species. Design, Synthesis, Structure, and Magnetism of Copper(II) Complexes with a Mixed Pyrazole-Imidazole Donor Set. Inorganic chemistry, 36(6), 1168-1175. https://doi.org/10.1021/ic961260d
Tabbì, Giovanni, et al. "High Superoxide Dismutase Activity of a Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(II) Species. Design, Synthesis, Structure, and Magnetism of Copper(II) Complexes with a Mixed Pyrazole-Imidazole Donor Set." Inorganic chemistry vol. 36,6 (1997): 1168-1175. doi: https://doi.org/10.1021/ic961260d
Tabbì G, Driessen WL, Reedijk J, Bonomo RP, Veldman N, Spek AL. High Superoxide Dismutase Activity of a Novel, Intramolecularly Imidazolato-Bridged Asymmetric Dicopper(II) Species. Design, Synthesis, Structure, and Magnetism of Copper(II) Complexes with a Mixed Pyrazole-Imidazole Donor Set. Inorg Chem. 1997 Mar 12;36(6):1168-1175. doi: 10.1021/ic961260d. PMID: 11669684.
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Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles.

Journal of inorganic biochemistry

Ikezaki A, Nakamura M.
PMID: 11330473
J Inorg Biochem. 2001 Mar;84(1):137-44. doi: 10.1016/s0162-0134(00)00205-1.

Reactions between (meso-tetraphenylporphyrinato)iron(III) perchlorate [Fe(tpp)]ClO4 and various imidazoles have been examined in CD2Cl2 solutions. 1H NMR analysis revealed the formation of three kinds of complex; mu-oxo dimer, mono-imidazole adduct, and bis-imidazole adduct. The product ratios changed to a great...

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Ikezaki A, Nakamura M. Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles. J Inorg Biochem. 2001;84(1):137-44doi: 10.1016/s0162-0134(00)00205-1.
Ikezaki, A., & Nakamura, M. (2001). Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles. Journal of inorganic biochemistry, 84(1), 137-44. https://doi.org/10.1016/s0162-0134(00)00205-1
Ikezaki, A, and Nakamura, M. "Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles." Journal of inorganic biochemistry vol. 84,1 (2001): 137-44. doi: https://doi.org/10.1016/s0162-0134(00)00205-1
Ikezaki A, Nakamura M. Formation of mu-oxo dimer by the reaction of (meso-tetraphenylporphyrinato)iron(III) with various imidazoles. J Inorg Biochem. 2001 Mar;84(1):137-44. doi: 10.1016/s0162-0134(00)00205-1. PMID: 11330473.
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Induced fit process in the selective distal binding of imidazoles in zinc(II) porphyrin receptors.

Inorganic chemistry

Paul D, Melin F, Hirtz C, Wytko J, Ochsenbein P, Bonin M, Schenk K, Maltese P, Weiss J.
PMID: 12793814
Inorg Chem. 2003 Jun 16;42(12):3779-87. doi: 10.1021/ic0341643.

The respective affinities of various imidazole derivatives, imidazole (ImH), 2-methylimidazole (2-MeImH), 2-phenylimidazole (2-PhImH), N-methylimidazole (N-MeIm), 2-methylbenzimidazole (2-MeBzImH), and 4,5-dimethylbenzimidazole (4,5-Me(2)BzImH), for two phenanthroline (Phen) strapped zinc(II) porphyrin receptors porphen-Zn 1-Zn and 2-Zn have been studied. The formation of a...

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Paul D, Melin F, Hirtz C, et al. Induced fit process in the selective distal binding of imidazoles in zinc(II) porphyrin receptors. Inorg Chem. 2003;42(12):3779-87doi: 10.1021/ic0341643.
Paul, D., Melin, F., Hirtz, C., Wytko, J., Ochsenbein, P., Bonin, M., Schenk, K., Maltese, P., & Weiss, J. (2003). Induced fit process in the selective distal binding of imidazoles in zinc(II) porphyrin receptors. Inorganic chemistry, 42(12), 3779-87. https://doi.org/10.1021/ic0341643
Paul, Dharam, et al. "Induced fit process in the selective distal binding of imidazoles in zinc(II) porphyrin receptors." Inorganic chemistry vol. 42,12 (2003): 3779-87. doi: https://doi.org/10.1021/ic0341643
Paul D, Melin F, Hirtz C, Wytko J, Ochsenbein P, Bonin M, Schenk K, Maltese P, Weiss J. Induced fit process in the selective distal binding of imidazoles in zinc(II) porphyrin receptors. Inorg Chem. 2003 Jun 16;42(12):3779-87. doi: 10.1021/ic0341643. PMID: 12793814.
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Design and synthesis of a self-assembled photochemical dyad based on selective imidazole recognition.

Inorganic chemistry

Paul D, Wytko JA, Koepf M, Weiss J.
PMID: 12099874
Inorg Chem. 2002 Jul 15;41(14):3699-704. doi: 10.1021/ic020043b.

The unique recognition properties of phenanthroline-strapped zinc porphyrin 1, which displays extremely high affinity for N-unsubstituted imidazoles, has been used as the driving force for the assembly of a photochemical dyad involving a zinc(II) porphyrin as energy donor and...

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Paul D, Wytko JA, Koepf M, et al. Design and synthesis of a self-assembled photochemical dyad based on selective imidazole recognition. Inorg Chem. 2002;41(14):3699-704doi: 10.1021/ic020043b.
Paul, D., Wytko, J. A., Koepf, M., & Weiss, J. (2002). Design and synthesis of a self-assembled photochemical dyad based on selective imidazole recognition. Inorganic chemistry, 41(14), 3699-704. https://doi.org/10.1021/ic020043b
Paul, Dharam, et al. "Design and synthesis of a self-assembled photochemical dyad based on selective imidazole recognition." Inorganic chemistry vol. 41,14 (2002): 3699-704. doi: https://doi.org/10.1021/ic020043b
Paul D, Wytko JA, Koepf M, Weiss J. Design and synthesis of a self-assembled photochemical dyad based on selective imidazole recognition. Inorg Chem. 2002 Jul 15;41(14):3699-704. doi: 10.1021/ic020043b. PMID: 12099874.
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Synthesis of Novel Chiral Diazole Derivative Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde.

The Journal of organic chemistry

Kotsuki H, Wakao M, Hayakawa H, Shimanouchi T, Shiro M.
PMID: 11667872
J Org Chem. 1996 Dec 13;61(25):8915-8920. doi: 10.1021/jo961388c.

The high-pressure-promoted reaction of epoxides with pyrazoles and imidazoles provided access to a variety of chiral diazole derivative ligands such as 11-23. Furthermore, chiral pyrazoles 26 and 27, which have a primary alcohol side chain, were also prepared from...

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Kotsuki H, Wakao M, Hayakawa H, et al. Synthesis of Novel Chiral Diazole Derivative Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde. J Org Chem. 1996;61(25):8915-8920doi: 10.1021/jo961388c.
Kotsuki, H., Wakao, M., Hayakawa, H., Shimanouchi, T., & Shiro, M. (1996). Synthesis of Novel Chiral Diazole Derivative Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde. The Journal of organic chemistry, 61(25), 8915-8920. https://doi.org/10.1021/jo961388c
Kotsuki, Hiyoshizo, et al. "Synthesis of Novel Chiral Diazole Derivative Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde." The Journal of organic chemistry vol. 61,25 (1996): 8915-8920. doi: https://doi.org/10.1021/jo961388c
Kotsuki H, Wakao M, Hayakawa H, Shimanouchi T, Shiro M. Synthesis of Novel Chiral Diazole Derivative Ligands for the Enantioselective Addition of Diethylzinc to Benzaldehyde. J Org Chem. 1996 Dec 13;61(25):8915-8920. doi: 10.1021/jo961388c. PMID: 11667872.
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Synthesis of substituted imidazoles via organocatalysis.

Organic letters

Frantz DE, Morency L, Soheili A, Murry JA, Grabowski EJ, Tillyer RD.
PMID: 14986989
Org Lett. 2004 Mar 04;6(5):843-6. doi: 10.1021/ol0498803.

A one-pot synthesis of substituted imidazoles is described. The cornerstone of this methodology involves the thiazolium-catalyzed addition of an aldehyde to an acyl imine to generate the corresponding alpha-ketoamide in situ followed by ring closure to the imidazole in...

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Frantz DE, Morency L, Soheili A, et al. Synthesis of substituted imidazoles via organocatalysis. Org Lett. 2004;6(5):843-6doi: 10.1021/ol0498803.
Frantz, D. E., Morency, L., Soheili, A., Murry, J. A., Grabowski, E. J., & Tillyer, R. D. (2004). Synthesis of substituted imidazoles via organocatalysis. Organic letters, 6(5), 843-6. https://doi.org/10.1021/ol0498803
Frantz, Doug E, et al. "Synthesis of substituted imidazoles via organocatalysis." Organic letters vol. 6,5 (2004): 843-6. doi: https://doi.org/10.1021/ol0498803
Frantz DE, Morency L, Soheili A, Murry JA, Grabowski EJ, Tillyer RD. Synthesis of substituted imidazoles via organocatalysis. Org Lett. 2004 Mar 04;6(5):843-6. doi: 10.1021/ol0498803. PMID: 14986989.
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