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Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides.

Journal of the American Chemical Society

Alford JS, Davies HM.
PMID: 24998910
J Am Chem Soc. 2014 Jul 23;136(29):10266-9. doi: 10.1021/ja5058967. Epub 2014 Jul 15.

An effective method for aminoacylation of indoles and pyrroles has been achieved. The transformation involves a multicomponent one-pot cascade reaction between indoles or pyrroles, ynol ethers, and sulfonyl azides, creating four different bonds regioselectively through N-sulfonyltriazole intermediates. The oxo-tryptamines...

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Alford JS, Davies HM. Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides. J Am Chem Soc. 2014;136(29):10266-9doi: 10.1021/ja5058967.
Alford, J. S., & Davies, H. M. (2014). Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides. Journal of the American Chemical Society, 136(29), 10266-9. https://doi.org/10.1021/ja5058967
Alford, Joshua S, and Davies, Huw M L. "Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides." Journal of the American Chemical Society vol. 136,29 (2014): 10266-9. doi: https://doi.org/10.1021/ja5058967
Alford JS, Davies HM. Mild aminoacylation of indoles and pyrroles through a three-component reaction with ynol ethers and sulfonyl azides. J Am Chem Soc. 2014 Jul 23;136(29):10266-9. doi: 10.1021/ja5058967. Epub 2014 Jul 15. PMID: 24998910.
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Antidepressive, anxiolytic, and antiaddictive effects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD): a systematic review of clinical trials published in the last 25 years.

Therapeutic advances in psychopharmacology

Dos Santos RG, Osório FL, Crippa JA, Riba J, Zuardi AW, Hallak JE.
PMID: 27354908
Ther Adv Psychopharmacol. 2016 Jun;6(3):193-213. doi: 10.1177/2045125316638008. Epub 2016 Mar 18.

To date, pharmacological treatments for mood and anxiety disorders and for drug dependence show limited efficacy, leaving a large number of patients suffering severe and persistent symptoms. Preliminary studies in animals and humans suggest that ayahuasca, psilocybin and lysergic...

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Dos Santos RG, Osório FL, Crippa JA, et al. Antidepressive, anxiolytic, and antiaddictive effects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD): a systematic review of clinical trials published in the last 25 years. Ther Adv Psychopharmacol. 2016;6(3):193-213doi: 10.1177/2045125316638008.
Dos Santos, R. G., Osório, F. L., Crippa, J. A., Riba, J., Zuardi, A. W., & Hallak, J. E. (2016). Antidepressive, anxiolytic, and antiaddictive effects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD): a systematic review of clinical trials published in the last 25 years. Therapeutic advances in psychopharmacology, 6(3), 193-213. https://doi.org/10.1177/2045125316638008
Dos Santos, Rafael G, et al. "Antidepressive, anxiolytic, and antiaddictive effects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD): a systematic review of clinical trials published in the last 25 years." Therapeutic advances in psychopharmacology vol. 6,3 (2016): 193-213. doi: https://doi.org/10.1177/2045125316638008
Dos Santos RG, Osório FL, Crippa JA, Riba J, Zuardi AW, Hallak JE. Antidepressive, anxiolytic, and antiaddictive effects of ayahuasca, psilocybin and lysergic acid diethylamide (LSD): a systematic review of clinical trials published in the last 25 years. Ther Adv Psychopharmacol. 2016 Jun;6(3):193-213. doi: 10.1177/2045125316638008. Epub 2016 Mar 18. PMID: 27354908; PMCID: PMC4910400.
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Enantiopure Tetrahydro-beta-carbolines via Pictet-Spengler Reactions with N-Sulfinyl Tryptamines.

Organic letters

Gremmen C, Willemse B, Wanner MJ, Koomen GJ.
PMID: 10891200
Org Lett. 2000 Jun 29;2(13):1955-1958. doi: 10.1021/ol006034t.

The influence of N-sulfinyl chiral auxiliaries on the stereochemistry of the Pictet-Spengler reaction has been investigated. From enantiopure (R)-N-p-toluenesulfinyltryptamine a new and efficient route to enantiopure tetrahydro-beta-carbolines has been established.

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Gremmen C, Willemse B, Wanner MJ, et al. Enantiopure Tetrahydro-beta-carbolines via Pictet-Spengler Reactions with N-Sulfinyl Tryptamines. Org Lett. 2000;2(13):1955-1958doi: 10.1021/ol006034t.
Gremmen, C., Willemse, B., Wanner, M. J., & Koomen, G. J. (2000). Enantiopure Tetrahydro-beta-carbolines via Pictet-Spengler Reactions with N-Sulfinyl Tryptamines. Organic letters, 2(13), 1955-1958. https://doi.org/10.1021/ol006034t
Gremmen, et al. "Enantiopure Tetrahydro-beta-carbolines via Pictet-Spengler Reactions with N-Sulfinyl Tryptamines." Organic letters vol. 2,13 (2000): 1955-1958. doi: https://doi.org/10.1021/ol006034t
Gremmen C, Willemse B, Wanner MJ, Koomen GJ. Enantiopure Tetrahydro-beta-carbolines via Pictet-Spengler Reactions with N-Sulfinyl Tryptamines. Org Lett. 2000 Jun 29;2(13):1955-1958. doi: 10.1021/ol006034t. PMID: 10891200.
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A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.

Talanta

Chen BH, Liu JT, Chen WX, Chen HM, Lin CH.
PMID: 18371669
Talanta. 2008 Jan 15;74(4):512-7. doi: 10.1016/j.talanta.2007.06.012. Epub 2007 Jun 19.

Certain characteristic fragmentations of tryptamines (indoleethylamine) and phenethylamines are described. Based on the GC-EI/MS, LC-ESI/MS and MALDI/TOFMS, the mass fragmentations of 13 standard compounds, including alpha-methyltryptamine (AMT), N,N-dimethyltryptamine (DMT), 5-methoxy-alpha-methyltryptamine (5-MeO-AMT), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-dibutyltryptamine (DBT), N,N-diisopropyltryptamine (DIPT),...

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Chen BH, Liu JT, Chen WX, et al. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta. 2007;74(4):512-7doi: 10.1016/j.talanta.2007.06.012.
Chen, B. H., Liu, J. T., Chen, W. X., Chen, H. M., & Lin, C. H. (2008). A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta, 74(4), 512-7. https://doi.org/10.1016/j.talanta.2007.06.012
Chen, Bo-Hong, et al. "A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation." Talanta vol. 74,4 (2008): 512-7. doi: https://doi.org/10.1016/j.talanta.2007.06.012
Chen BH, Liu JT, Chen WX, Chen HM, Lin CH. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta. 2008 Jan 15;74(4):512-7. doi: 10.1016/j.talanta.2007.06.012. Epub 2007 Jun 19. PMID: 18371669.
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Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa.

Planta medica

Prakash A, Varma RK, Ghosal S.
PMID: 17402065
Planta Med. 1981 Dec;43(4):384-8. doi: 10.1055/s-2007-971529.

Three types of alkaloidal constituents, viz., beta-phenethylamines, quinazolines and carboxylated tryptamines, in addition to choline and betaine have been isolated from Sida acuta Burm., S. humilis Willd., S. rhombifolia L., and S. spinosa L. and characterized by their physical...

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Prakash A, Varma RK, Ghosal S. Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta Med. 1981;43(4):384-8doi: 10.1055/s-2007-971529.
Prakash, A., Varma, R. K., & Ghosal, S. (1981). Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta medica, 43(4), 384-8. https://doi.org/10.1055/s-2007-971529
Prakash, A, et al. "Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa." Planta medica vol. 43,4 (1981): 384-8. doi: https://doi.org/10.1055/s-2007-971529
Prakash A, Varma RK, Ghosal S. Alkaloid constituents of Sida acuta, S. humilis, S. rhombifolia and S. spinosa. Planta Med. 1981 Dec;43(4):384-8. doi: 10.1055/s-2007-971529. PMID: 17402065.
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Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides.

The Journal of organic chemistry

Liang K, Tong X, Li T, Shi B, Wang H, Yan P, Xia C.
PMID: 30091607
J Org Chem. 2018 Sep 21;83(18):10948-10958. doi: 10.1021/acs.joc.8b01597. Epub 2018 Aug 23.

Nitroxides can absorb both ultraviolet (UV) and visible light, and their electron can be excited from the π-bonding orbital to the antibonding π* orbital or the n-bonding orbital to the antibonding π* orbital, respectively. Despite the reported UV-induced hydrogen...

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Liang K, Tong X, Li T, et al. Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides. J Org Chem. 2018;83(18):10948-10958doi: 10.1021/acs.joc.8b01597.
Liang, K., Tong, X., Li, T., Shi, B., Wang, H., Yan, P., & Xia, C. (2018). Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides. The Journal of organic chemistry, 83(18), 10948-10958. https://doi.org/10.1021/acs.joc.8b01597
Liang, Kangjiang, et al. "Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides." The Journal of organic chemistry vol. 83,18 (2018): 10948-10958. doi: https://doi.org/10.1021/acs.joc.8b01597
Liang K, Tong X, Li T, Shi B, Wang H, Yan P, Xia C. Enantioselective Radical Cyclization of Tryptamines by Visible Light-Excited Nitroxides. J Org Chem. 2018 Sep 21;83(18):10948-10958. doi: 10.1021/acs.joc.8b01597. Epub 2018 Aug 23. PMID: 30091607.
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Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones.

The Journal of organic chemistry

Han H, Yang SD, Xia JB.
PMID: 30793907
J Org Chem. 2019 Mar 15;84(6):3357-3369. doi: 10.1021/acs.joc.8b03266. Epub 2019 Feb 28.

The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.

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Han H, Yang SD, Xia JB. Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones. J Org Chem. 2019;84(6):3357-3369doi: 10.1021/acs.joc.8b03266.
Han, H., Yang, S. D., & Xia, J. B. (2019). Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones. The Journal of organic chemistry, 84(6), 3357-3369. https://doi.org/10.1021/acs.joc.8b03266
Han, Hui, et al. "Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones." The Journal of organic chemistry vol. 84,6 (2019): 3357-3369. doi: https://doi.org/10.1021/acs.joc.8b03266
Han H, Yang SD, Xia JB. Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones. J Org Chem. 2019 Mar 15;84(6):3357-3369. doi: 10.1021/acs.joc.8b03266. Epub 2019 Feb 28. PMID: 30793907.
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Ni-Catalyzed Intermolecular Allylic Dearomatization Reaction of Tryptophols and Tryptamines.

Organic letters

Zhang HJ, Gu Q, You SL.
PMID: 31714790
Org Lett. 2019 Dec 06;21(23):9420-9424. doi: 10.1021/acs.orglett.9b03633. Epub 2019 Nov 12.

An efficient synthesis of pyrrolidinoindolines and tetrahydrofuranoindolines was achieved via Ni-catalyzed allylic dearomatization reactions of tryptophols and tryptamines. In the presence of 13 mol % of Ni(cod)

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Zhang HJ, Gu Q, You SL. Ni-Catalyzed Intermolecular Allylic Dearomatization Reaction of Tryptophols and Tryptamines. Org Lett. 2019;21(23):9420-9424doi: 10.1021/acs.orglett.9b03633.
Zhang, H. J., Gu, Q., & You, S. L. (2019). Ni-Catalyzed Intermolecular Allylic Dearomatization Reaction of Tryptophols and Tryptamines. Organic letters, 21(23), 9420-9424. https://doi.org/10.1021/acs.orglett.9b03633
Zhang, Hui-Jun, et al. "Ni-Catalyzed Intermolecular Allylic Dearomatization Reaction of Tryptophols and Tryptamines." Organic letters vol. 21,23 (2019): 9420-9424. doi: https://doi.org/10.1021/acs.orglett.9b03633
Zhang HJ, Gu Q, You SL. Ni-Catalyzed Intermolecular Allylic Dearomatization Reaction of Tryptophols and Tryptamines. Org Lett. 2019 Dec 06;21(23):9420-9424. doi: 10.1021/acs.orglett.9b03633. Epub 2019 Nov 12. PMID: 31714790.
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Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs.

Forensic science international

Niebel A, Pragst F, Krumbiegel F, Hartwig S.
PMID: 34923263
Forensic Sci Int. 2021 Dec 10;331:111148. doi: 10.1016/j.forsciint.2021.111148. Epub 2021 Dec 10.

BACKGROUND: Hair analysis of parents and their children was regularly used since 2011 as a diagnostic tool in a social support project for families with known or suspected abuse of conventional illegal drugs and revealed a high incidence of...

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Niebel A, Pragst F, Krumbiegel F, et al. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic Sci Int. 2021;331:111148doi: 10.1016/j.forsciint.2021.111148.
Niebel, A., Pragst, F., Krumbiegel, F., & Hartwig, S. (2021). Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic science international, 331111148. https://doi.org/10.1016/j.forsciint.2021.111148
Niebel, André, et al. "Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs." Forensic science international vol. 331 (2021): 111148. doi: https://doi.org/10.1016/j.forsciint.2021.111148
Niebel A, Pragst F, Krumbiegel F, Hartwig S. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic Sci Int. 2021 Dec 10;331:111148. doi: 10.1016/j.forsciint.2021.111148. Epub 2021 Dec 10. PMID: 34923263.
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Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs.

Forensic science international

Niebel A, Pragst F, Krumbiegel F, Hartwig S.
PMID: 34923263
Forensic Sci Int. 2021 Dec 10;331:111148. doi: 10.1016/j.forsciint.2021.111148. Epub 2021 Dec 10.

BACKGROUND: Hair analysis of parents and their children was regularly used since 2011 as a diagnostic tool in a social support project for families with known or suspected abuse of conventional illegal drugs and revealed a high incidence of...

Cite
Niebel A, Pragst F, Krumbiegel F, et al. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic Sci Int. 2021;331:111148doi: 10.1016/j.forsciint.2021.111148.
Niebel, A., Pragst, F., Krumbiegel, F., & Hartwig, S. (2021). Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic science international, 331111148. https://doi.org/10.1016/j.forsciint.2021.111148
Niebel, André, et al. "Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs." Forensic science international vol. 331 (2021): 111148. doi: https://doi.org/10.1016/j.forsciint.2021.111148
Niebel A, Pragst F, Krumbiegel F, Hartwig S. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic Sci Int. 2021 Dec 10;331:111148. doi: 10.1016/j.forsciint.2021.111148. Epub 2021 Dec 10. PMID: 34923263.
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Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs.

Forensic science international

Niebel A, Pragst F, Krumbiegel F, Hartwig S.
PMID: 34923263
Forensic Sci Int. 2021 Dec 10;331:111148. doi: 10.1016/j.forsciint.2021.111148. Epub 2021 Dec 10.

BACKGROUND: Hair analysis of parents and their children was regularly used since 2011 as a diagnostic tool in a social support project for families with known or suspected abuse of conventional illegal drugs and revealed a high incidence of...

Cite
Niebel A, Pragst F, Krumbiegel F, et al. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic Sci Int. 2021;331:111148doi: 10.1016/j.forsciint.2021.111148.
Niebel, A., Pragst, F., Krumbiegel, F., & Hartwig, S. (2021). Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic science international, 331111148. https://doi.org/10.1016/j.forsciint.2021.111148
Niebel, André, et al. "Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs." Forensic science international vol. 331 (2021): 111148. doi: https://doi.org/10.1016/j.forsciint.2021.111148
Niebel A, Pragst F, Krumbiegel F, Hartwig S. Prevalence of cathinones and other new psychoactive substances in hair of parents and children of families with known or suspected parental abuse of conventional illegal drugs. Forensic Sci Int. 2021 Dec 10;331:111148. doi: 10.1016/j.forsciint.2021.111148. Epub 2021 Dec 10. PMID: 34923263.
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The crystalline forms of nine hydrochloride salts of substituted tryptamines.

Acta crystallographica. Section C, Structural chemistry

Pham DNK, Belanger ZS, Chadeayne AR, Golen JA, Manke DR.
PMID: 34607984
Acta Crystallogr C Struct Chem. 2021 Oct 01;77:615-620. doi: 10.1107/S2053229621008950. Epub 2021 Sep 10.

The crystal structures of the hydrochloride salts of nine substituted tryptamines, namely, 1-methyltryptammonium chloride, C

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Pham DNK, Belanger ZS, Chadeayne AR, et al. The crystalline forms of nine hydrochloride salts of substituted tryptamines. Acta Crystallogr C Struct Chem. 2021;77:615-620doi: 10.1107/S2053229621008950.
Pham, D. N. K., Belanger, Z. S., Chadeayne, A. R., Golen, J. A., & Manke, D. R. (2021). The crystalline forms of nine hydrochloride salts of substituted tryptamines. Acta crystallographica. Section C, Structural chemistry, 77615-620. https://doi.org/10.1107/S2053229621008950
Pham, Duyen N K, et al. "The crystalline forms of nine hydrochloride salts of substituted tryptamines." Acta crystallographica. Section C, Structural chemistry vol. 77 (2021): 615-620. doi: https://doi.org/10.1107/S2053229621008950
Pham DNK, Belanger ZS, Chadeayne AR, Golen JA, Manke DR. The crystalline forms of nine hydrochloride salts of substituted tryptamines. Acta Crystallogr C Struct Chem. 2021 Oct 01;77:615-620. doi: 10.1107/S2053229621008950. Epub 2021 Sep 10. PMID: 34607984.
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