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Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines.

Organic letters

Adiyala PR, Mani GS, Nanubolu JB, Shekar KC, Maurya RA.
PMID: 26308984
Org Lett. 2015 Sep 04;17(17):4308-11. doi: 10.1021/acs.orglett.5b02124. Epub 2015 Aug 26.

A novel strategy for the synthesis of imidazo[1,2-a]pyridines via efficient catalyst/metal-free annulations of α-keto vinyl azides and 2-aminopyridines is described. Several imidazo[1,2-a]pyridines were synthesized from readily available vinyl azides and 2-aminopyridines and obtained in highly pure form by simply...

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Adiyala PR, Mani GS, Nanubolu JB, et al. Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines. Org Lett. 2015;17(17):4308-11doi: 10.1021/acs.orglett.5b02124.
Adiyala, P. R., Mani, G. S., Nanubolu, J. B., Shekar, K. C., & Maurya, R. A. (2015). Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines. Organic letters, 17(17), 4308-11. https://doi.org/10.1021/acs.orglett.5b02124
Adiyala, Praveen Reddy, et al. "Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines." Organic letters vol. 17,17 (2015): 4308-11. doi: https://doi.org/10.1021/acs.orglett.5b02124
Adiyala PR, Mani GS, Nanubolu JB, Shekar KC, Maurya RA. Access to Imidazo[1,2-a]pyridines via Annulation of α-Keto Vinyl Azides and 2-Aminopyridines. Org Lett. 2015 Sep 04;17(17):4308-11. doi: 10.1021/acs.orglett.5b02124. Epub 2015 Aug 26. PMID: 26308984.
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4-aminopyridine improves lower urinary tract symptoms in a patient with benign prostatic hyperplasia and downbeat nystagmus syndrome.

International neurourology journal

Strupp M, Feil K, Bardins S, Waidelich R.
PMID: 25558420
Int Neurourol J. 2014 Dec;18(4):221-5. doi: 10.5213/inj.2014.18.4.221. Epub 2014 Dec 29.

Aminopyridines are potassium channel blockers that increase the excitability of nerve cells and axons; therefore, they are widely used to treat different neurological disorders. Here we present a patient with idiopathic downbeat nystagmus and lower urinary tract symptoms (LUTS)...

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Strupp M, Feil K, Bardins S, et al. 4-aminopyridine improves lower urinary tract symptoms in a patient with benign prostatic hyperplasia and downbeat nystagmus syndrome. Int Neurourol J. 2014;18(4):221-5doi: 10.5213/inj.2014.18.4.221.
Strupp, M., Feil, K., Bardins, S., & Waidelich, R. (2014). 4-aminopyridine improves lower urinary tract symptoms in a patient with benign prostatic hyperplasia and downbeat nystagmus syndrome. International neurourology journal, 18(4), 221-5. https://doi.org/10.5213/inj.2014.18.4.221
Strupp, Michael, et al. "4-aminopyridine improves lower urinary tract symptoms in a patient with benign prostatic hyperplasia and downbeat nystagmus syndrome." International neurourology journal vol. 18,4 (2014): 221-5. doi: https://doi.org/10.5213/inj.2014.18.4.221
Strupp M, Feil K, Bardins S, Waidelich R. 4-aminopyridine improves lower urinary tract symptoms in a patient with benign prostatic hyperplasia and downbeat nystagmus syndrome. Int Neurourol J. 2014 Dec;18(4):221-5. doi: 10.5213/inj.2014.18.4.221. Epub 2014 Dec 29. PMID: 25558420; PMCID: PMC4280442.
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Selenium-Catalyzed Oxidative C(sp(2))-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles.

Organic letters

Ortgies S, Breder A.
PMID: 25997578
Org Lett. 2015 Jun 05;17(11):2748-51. doi: 10.1021/acs.orglett.5b01156. Epub 2015 May 22.

A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp(2))-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily...

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Ortgies S, Breder A. Selenium-Catalyzed Oxidative C(sp(2))-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles. Org Lett. 2015;17(11):2748-51doi: 10.1021/acs.orglett.5b01156.
Ortgies, S., & Breder, A. (2015). Selenium-Catalyzed Oxidative C(sp(2))-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles. Organic letters, 17(11), 2748-51. https://doi.org/10.1021/acs.orglett.5b01156
Ortgies, Stefan, and Breder, Alexander. "Selenium-Catalyzed Oxidative C(sp(2))-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles." Organic letters vol. 17,11 (2015): 2748-51. doi: https://doi.org/10.1021/acs.orglett.5b01156
Ortgies S, Breder A. Selenium-Catalyzed Oxidative C(sp(2))-H Amination of Alkenes Exemplified in the Expedient Synthesis of (Aza-)Indoles. Org Lett. 2015 Jun 05;17(11):2748-51. doi: 10.1021/acs.orglett.5b01156. Epub 2015 May 22. PMID: 25997578.
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Rh(iii)-catalyzed 7-azaindole synthesis via C-H activation/annulative coupling of aminopyridines with alkynes.

Chemical communications (Cambridge, England)

Kim Y, Hong S.
PMID: 26077013
Chem Commun (Camb). 2015 Jun 30;51(56):11202-5. doi: 10.1039/c5cc03497c.

An efficient Rh(iii)-catalyzed 7-azaindole synthesis was developed via C-H activation/annulative coupling of aminopyridines with alkynes. The reaction was highly regioselective and tolerated various functional groups, permitting the construction of various 7-azaindoles.

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Kim Y, Hong S. Rh(iii)-catalyzed 7-azaindole synthesis via C-H activation/annulative coupling of aminopyridines with alkynes. Chem Commun (Camb). 2015;51(56):11202-5doi: 10.1039/c5cc03497c.
Kim, Y., & Hong, S. (2015). Rh(iii)-catalyzed 7-azaindole synthesis via C-H activation/annulative coupling of aminopyridines with alkynes. Chemical communications (Cambridge, England), 51(56), 11202-5. https://doi.org/10.1039/c5cc03497c
Kim, Yechan, and Hong, Sungwoo. "Rh(iii)-catalyzed 7-azaindole synthesis via C-H activation/annulative coupling of aminopyridines with alkynes." Chemical communications (Cambridge, England) vol. 51,56 (2015): 11202-5. doi: https://doi.org/10.1039/c5cc03497c
Kim Y, Hong S. Rh(iii)-catalyzed 7-azaindole synthesis via C-H activation/annulative coupling of aminopyridines with alkynes. Chem Commun (Camb). 2015 Jun 30;51(56):11202-5. doi: 10.1039/c5cc03497c. PMID: 26077013.
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Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles.

The Journal of organic chemistry

Zhang J, Lu X, Li T, Wang S, Zhong G.
PMID: 28429945
J Org Chem. 2017 May 19;82(10):5222-5229. doi: 10.1021/acs.joc.7b00480. Epub 2017 Apr 27.

A catalytic oxidative cyclization of 2-aminopyridines or 2-aminobenzothiazole with 2-phenoxyacetophenones (a kind of lignin platform compound) was developed, efficiently providing valuable 3-phenoxy imidazo[1,2-a]pyridines or 3-phenoxy benzo[d]imidazo[2,1-b]thiazoles. The reaction was realized under oxygen by simply using inexpensive CuI as the...

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Zhang J, Lu X, Li T, et al. Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. J Org Chem. 2017;82(10):5222-5229doi: 10.1021/acs.joc.7b00480.
Zhang, J., Lu, X., Li, T., Wang, S., & Zhong, G. (2017). Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. The Journal of organic chemistry, 82(10), 5222-5229. https://doi.org/10.1021/acs.joc.7b00480
Zhang, Jian, et al. "Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles." The Journal of organic chemistry vol. 82,10 (2017): 5222-5229. doi: https://doi.org/10.1021/acs.joc.7b00480
Zhang J, Lu X, Li T, Wang S, Zhong G. Copper-Catalyzed Oxidative Cyclization of 2-Amino-azaarenes with Lignin Models: Synthesis of 3-Phenoxy Imidazo Heterocycles. J Org Chem. 2017 May 19;82(10):5222-5229. doi: 10.1021/acs.joc.7b00480. Epub 2017 Apr 27. PMID: 28429945.
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CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines.

Organic letters

Huo C, Tang J, Xie H, Wang Y, Dong J.
PMID: 26882001
Org Lett. 2016 Mar 04;18(5):1016-9. doi: 10.1021/acs.orglett.6b00137. Epub 2016 Feb 16.

The carbon tetrabromide mediated oxidative carbon-nitrogen bond formation of 2-aminopyridines or 2-aminopyrimidines with β-keto esters or 1,3-diones, leading to a variety of complex imidazo[1,2-α]pyridines or imidazo[1,2-α]pyrimidines, is reported. The reactions were realized under mild and metal-free conditions.

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Huo C, Tang J, Xie H, et al. CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines. Org Lett. 2016;18(5):1016-9doi: 10.1021/acs.orglett.6b00137.
Huo, C., Tang, J., Xie, H., Wang, Y., & Dong, J. (2016). CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines. Organic letters, 18(5), 1016-9. https://doi.org/10.1021/acs.orglett.6b00137
Huo, Congde, et al. "CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines." Organic letters vol. 18,5 (2016): 1016-9. doi: https://doi.org/10.1021/acs.orglett.6b00137
Huo C, Tang J, Xie H, Wang Y, Dong J. CBr4 Mediated Oxidative C-N Bond Formation: Applied in the Synthesis of Imidazo[1,2-α]pyridines and Imidazo[1,2-α]pyrimidines. Org Lett. 2016 Mar 04;18(5):1016-9. doi: 10.1021/acs.orglett.6b00137. Epub 2016 Feb 16. PMID: 26882001.
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Self-complementarity of oligo-2-aminopyridines: a new class of hydrogen-bonded ladders.

Journal of the American Chemical Society

Leung MK, Mandal AB, Wang CC, Lee GH, Peng SM, Cheng HL, Her GR, Chao I, Lu HF, Sun YC, Shiao MY, Chou PT.
PMID: 11960458
J Am Chem Soc. 2002 Apr 24;124(16):4287-97. doi: 10.1021/ja011679p.

A new class of hydrogen-bonded ladders based on hydrogen-bonded dimerization of oligo-alpha-aminopryidines has been demonstrated. Jorgensen's model can be successfully applied to this hydrogen-bonding system in nonpolar solvents. The results show the competitive enthalpy/entropy compensation relationship upon dimerization. Although...

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Leung MK, Mandal AB, Wang CC, et al. Self-complementarity of oligo-2-aminopyridines: a new class of hydrogen-bonded ladders. J Am Chem Soc. 2002;124(16):4287-97doi: 10.1021/ja011679p.
Leung, M. K., Mandal, A. B., Wang, C. C., Lee, G. H., Peng, S. M., Cheng, H. L., Her, G. R., Chao, I., Lu, H. F., Sun, Y. C., Shiao, M. Y., & Chou, P. T. (2002). Self-complementarity of oligo-2-aminopyridines: a new class of hydrogen-bonded ladders. Journal of the American Chemical Society, 124(16), 4287-97. https://doi.org/10.1021/ja011679p
Leung, Man-kit, et al. "Self-complementarity of oligo-2-aminopyridines: a new class of hydrogen-bonded ladders." Journal of the American Chemical Society vol. 124,16 (2002): 4287-97. doi: https://doi.org/10.1021/ja011679p
Leung MK, Mandal AB, Wang CC, Lee GH, Peng SM, Cheng HL, Her GR, Chao I, Lu HF, Sun YC, Shiao MY, Chou PT. Self-complementarity of oligo-2-aminopyridines: a new class of hydrogen-bonded ladders. J Am Chem Soc. 2002 Apr 24;124(16):4287-97. doi: 10.1021/ja011679p. PMID: 11960458.
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Chemistry of stable iminopropadienones, RN=C=C=C=O.

The Journal of organic chemistry

Bibas H, Moloney DW, Neumann R, Shtaiwi M, Bernhardt PV, Wentrup C.
PMID: 11950308
J Org Chem. 2002 Apr 19;67(8):2619-31. doi: 10.1021/jo0110552.

The synthesis, spectroscopic properties, and chemical reactions of the stable (neopentylimino)-, (mesitylimino)-, and (o-tert-butylphenylimino)propadienones (6) are reported. Nucleophilic addition of amines affords the malonic amidoamidines 7 and 8. 3,5-Dimethylpyrazole reacts analogously to form 9b. Addition of 1,2-dimethylhydrazine produces pyrazolinones...

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Bibas H, Moloney DW, Neumann R, et al. Chemistry of stable iminopropadienones, RN=C=C=C=O. J Org Chem. 2002;67(8):2619-31doi: 10.1021/jo0110552.
Bibas, H., Moloney, D. W., Neumann, R., Shtaiwi, M., Bernhardt, P. V., & Wentrup, C. (2002). Chemistry of stable iminopropadienones, RN=C=C=C=O. The Journal of organic chemistry, 67(8), 2619-31. https://doi.org/10.1021/jo0110552
Bibas, Hervé, et al. "Chemistry of stable iminopropadienones, RN=C=C=C=O." The Journal of organic chemistry vol. 67,8 (2002): 2619-31. doi: https://doi.org/10.1021/jo0110552
Bibas H, Moloney DW, Neumann R, Shtaiwi M, Bernhardt PV, Wentrup C. Chemistry of stable iminopropadienones, RN=C=C=C=O. J Org Chem. 2002 Apr 19;67(8):2619-31. doi: 10.1021/jo0110552. PMID: 11950308.
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Interaction of 2-Amino-, 3-Amino-, and 4-Aminopyridines with Chromium and Manganese Ferrocyanides.

Journal of colloid and interface science

Alam T, Tarannum H, Kumar N, Kamaluddin.
PMID: 10708502
J Colloid Interface Sci. 2000 Apr 01;224(1):133-139. doi: 10.1006/jcis.1999.6681.

The present investigation deals with the interaction of 2-aminopyridine, 3-aminopyridine, and 4-aminopyridine with chromium and manganese ferrocyanides. Chromium ferrocyanide possesses better adsorbing properties than manganese ferrocyanide. Maximum uptake was observed at neutral pH (pH 7.0). The adsorption data obtained...

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Alam T, Tarannum H, Kumar N, et al. Interaction of 2-Amino-, 3-Amino-, and 4-Aminopyridines with Chromium and Manganese Ferrocyanides. J Colloid Interface Sci. 2000;224(1):133-139doi: 10.1006/jcis.1999.6681.
Alam, T., Tarannum, H., Kumar, N., & Kamaluddin. (2000). Interaction of 2-Amino-, 3-Amino-, and 4-Aminopyridines with Chromium and Manganese Ferrocyanides. Journal of colloid and interface science, 224(1), 133-139. https://doi.org/10.1006/jcis.1999.6681
Alam, et al. "Interaction of 2-Amino-, 3-Amino-, and 4-Aminopyridines with Chromium and Manganese Ferrocyanides." Journal of colloid and interface science vol. 224,1 (2000): 133-139. doi: https://doi.org/10.1006/jcis.1999.6681
Alam T, Tarannum H, Kumar N, Kamaluddin. Interaction of 2-Amino-, 3-Amino-, and 4-Aminopyridines with Chromium and Manganese Ferrocyanides. J Colloid Interface Sci. 2000 Apr 01;224(1):133-139. doi: 10.1006/jcis.1999.6681. PMID: 10708502.
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Evaluation of the potential of chitosan hydrogels to extract polar organic species from nonpolar organic solvents: application to the extraction of aminopyridines from hexane.

Journal of colloid and interface science

de Fávere VT, Hinze WL.
PMID: 18992899
J Colloid Interface Sci. 2009 Feb 01;330(1):38-44. doi: 10.1016/j.jcis.2008.10.035. Epub 2008 Nov 06.

The extraction of a series of aminopyridines (APs) utilizing chitosan hydrogels in hexane was investigated. The chitosan hydrogel was prepared using glutaraldehyde as a cross-linking agent. Experiments were carried out to determine the maximum extraction efficiency, distribution coefficient, sorption...

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de Fávere VT, Hinze WL. Evaluation of the potential of chitosan hydrogels to extract polar organic species from nonpolar organic solvents: application to the extraction of aminopyridines from hexane. J Colloid Interface Sci. 2008;330(1):38-44doi: 10.1016/j.jcis.2008.10.035.
de Fávere, V. T., & Hinze, W. L. (2009). Evaluation of the potential of chitosan hydrogels to extract polar organic species from nonpolar organic solvents: application to the extraction of aminopyridines from hexane. Journal of colloid and interface science, 330(1), 38-44. https://doi.org/10.1016/j.jcis.2008.10.035
de Fávere, Valfredo T, and Hinze, Willie L. "Evaluation of the potential of chitosan hydrogels to extract polar organic species from nonpolar organic solvents: application to the extraction of aminopyridines from hexane." Journal of colloid and interface science vol. 330,1 (2009): 38-44. doi: https://doi.org/10.1016/j.jcis.2008.10.035
de Fávere VT, Hinze WL. Evaluation of the potential of chitosan hydrogels to extract polar organic species from nonpolar organic solvents: application to the extraction of aminopyridines from hexane. J Colloid Interface Sci. 2009 Feb 01;330(1):38-44. doi: 10.1016/j.jcis.2008.10.035. Epub 2008 Nov 06. PMID: 18992899.
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Cosorption of Zn(II) and 2-, 3-, or 4-aminopyridine by montmorillonite.

Journal of colloid and interface science

Ikhsan J, Angove MJ, Johnson BB, Wells JD.
PMID: 15780275
J Colloid Interface Sci. 2005 Apr 15;284(2):400-7. doi: 10.1016/j.jcis.2004.10.059.

Data from acid-base titrations at 25 degrees C of Zn(NO(3))(2) and 2-, 3-, or 4-aminopyridine in 10 mM KNO(3) as background electrolyte suggested that soluble complexes ZnL(2+) and Zn(OH)L(+) form, where L represents aminopyridine. Zinc-hydroxyaminopyridine complexes have not been...

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Ikhsan J, Angove MJ, Johnson BB, et al. Cosorption of Zn(II) and 2-, 3-, or 4-aminopyridine by montmorillonite. J Colloid Interface Sci. 2005;284(2):400-7doi: 10.1016/j.jcis.2004.10.059.
Ikhsan, J., Angove, M. J., Johnson, B. B., & Wells, J. D. (2005). Cosorption of Zn(II) and 2-, 3-, or 4-aminopyridine by montmorillonite. Journal of colloid and interface science, 284(2), 400-7. https://doi.org/10.1016/j.jcis.2004.10.059
Ikhsan, Jaslin, et al. "Cosorption of Zn(II) and 2-, 3-, or 4-aminopyridine by montmorillonite." Journal of colloid and interface science vol. 284,2 (2005): 400-7. doi: https://doi.org/10.1016/j.jcis.2004.10.059
Ikhsan J, Angove MJ, Johnson BB, Wells JD. Cosorption of Zn(II) and 2-, 3-, or 4-aminopyridine by montmorillonite. J Colloid Interface Sci. 2005 Apr 15;284(2):400-7. doi: 10.1016/j.jcis.2004.10.059. PMID: 15780275.
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Reversible chain transfer between organoyttrium cations and aluminum: synthesis of aluminum-terminated polyethylene with extremely narrow molecular-weight distribution.

Chemistry (Weinheim an der Bergstrasse, Germany)

Kretschmer WP, Meetsma A, Hessen B, Schmalz T, Qayyum S, Kempe R.
PMID: 17009362
Chemistry. 2006 Dec 04;12(35):8969-78. doi: 10.1002/chem.200600660.

Aminopyridinato-ligand-stabilized organoyttrium cations are accessible in very good yield through alkane elimination from trialkyl yttrium complexes with sterically demanding aminopyridines, followed by abstraction of one of the two alkyl functions using ammonium borates. At 80 degrees C and in...

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Kretschmer WP, Meetsma A, Hessen B, et al. Reversible chain transfer between organoyttrium cations and aluminum: synthesis of aluminum-terminated polyethylene with extremely narrow molecular-weight distribution. Chemistry. 2006;12(35):8969-78doi: 10.1002/chem.200600660.
Kretschmer, W. P., Meetsma, A., Hessen, B., Schmalz, T., Qayyum, S., & Kempe, R. (2006). Reversible chain transfer between organoyttrium cations and aluminum: synthesis of aluminum-terminated polyethylene with extremely narrow molecular-weight distribution. Chemistry (Weinheim an der Bergstrasse, Germany), 12(35), 8969-78. https://doi.org/10.1002/chem.200600660
Kretschmer, Winfried P, et al. "Reversible chain transfer between organoyttrium cations and aluminum: synthesis of aluminum-terminated polyethylene with extremely narrow molecular-weight distribution." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 12,35 (2006): 8969-78. doi: https://doi.org/10.1002/chem.200600660
Kretschmer WP, Meetsma A, Hessen B, Schmalz T, Qayyum S, Kempe R. Reversible chain transfer between organoyttrium cations and aluminum: synthesis of aluminum-terminated polyethylene with extremely narrow molecular-weight distribution. Chemistry. 2006 Dec 04;12(35):8969-78. doi: 10.1002/chem.200600660. PMID: 17009362.
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