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Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst.

Journal of the American Chemical Society

Zhang J, Chen H, Lin C, Liu Z, Wang C, Zhang Y.
PMID: 26389708
J Am Chem Soc. 2015 Oct 14;137(40):12990-6. doi: 10.1021/jacs.5b07424. Epub 2015 Oct 01.

A new method of cobalt-catalyzed synthesis of pyrrolidinones from aliphatic amides and terminal alkynes was discovered through a C-H bond functionalization process on unactivated sp(3) carbons with the silver cocatalyst using a bidentate auxiliary. For the first time, a...

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Zhang J, Chen H, Lin C, et al. Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst. J Am Chem Soc. 2015;137(40):12990-6doi: 10.1021/jacs.5b07424.
Zhang, J., Chen, H., Lin, C., Liu, Z., Wang, C., & Zhang, Y. (2015). Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst. Journal of the American Chemical Society, 137(40), 12990-6. https://doi.org/10.1021/jacs.5b07424
Zhang, Jitan, et al. "Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst." Journal of the American Chemical Society vol. 137,40 (2015): 12990-6. doi: https://doi.org/10.1021/jacs.5b07424
Zhang J, Chen H, Lin C, Liu Z, Wang C, Zhang Y. Cobalt-Catalyzed Cyclization of Aliphatic Amides and Terminal Alkynes with Silver-Cocatalyst. J Am Chem Soc. 2015 Oct 14;137(40):12990-6. doi: 10.1021/jacs.5b07424. Epub 2015 Oct 01. PMID: 26389708.
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Radical carboazidation: expedient assembly of the core structure of various alkaloid families.

The Journal of organic chemistry

Panchaud P, Ollivier C, Renaud P, Zigmantas S.
PMID: 15074924
J Org Chem. 2004 Apr 16;69(8):2755-9. doi: 10.1021/jo035843y.

A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of...

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Panchaud P, Ollivier C, Renaud P, et al. Radical carboazidation: expedient assembly of the core structure of various alkaloid families. J Org Chem. 2004;69(8):2755-9doi: 10.1021/jo035843y.
Panchaud, P., Ollivier, C., Renaud, P., & Zigmantas, S. (2004). Radical carboazidation: expedient assembly of the core structure of various alkaloid families. The Journal of organic chemistry, 69(8), 2755-9. https://doi.org/10.1021/jo035843y
Panchaud, Philippe, et al. "Radical carboazidation: expedient assembly of the core structure of various alkaloid families." The Journal of organic chemistry vol. 69,8 (2004): 2755-9. doi: https://doi.org/10.1021/jo035843y
Panchaud P, Ollivier C, Renaud P, Zigmantas S. Radical carboazidation: expedient assembly of the core structure of various alkaloid families. J Org Chem. 2004 Apr 16;69(8):2755-9. doi: 10.1021/jo035843y. PMID: 15074924.
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Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate.

Beilstein journal of organic chemistry

Gao H, Sun J, Yan CG.
PMID: 24454573
Beilstein J Org Chem. 2013 Dec 27;9:2934-9. doi: 10.3762/bjoc.9.330. eCollection 2013 Dec 27.

The four-component reaction of 2-aminobenzothiazole, aromatic aldehydes, acetylenedicarboxylate and piperidine or pyrrolidine in ethanol afforded the functionalized 2-pyrrolidinones containing both benzothiazolyl and piperidinyl (or pyrrolidinyl) units in good yields. On the other hand, the similar four-component reactions resulted in...

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Gao H, Sun J, Yan CG. Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate. Beilstein J Org Chem. 2013;9:2934-9doi: 10.3762/bjoc.9.330.
Gao, H., Sun, J., & Yan, C. G. (2013). Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate. Beilstein journal of organic chemistry, 92934-9. https://doi.org/10.3762/bjoc.9.330
Gao, Hong, et al. "Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate." Beilstein journal of organic chemistry vol. 9 (2013): 2934-9. doi: https://doi.org/10.3762/bjoc.9.330
Gao H, Sun J, Yan CG. Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate. Beilstein J Org Chem. 2013 Dec 27;9:2934-9. doi: 10.3762/bjoc.9.330. eCollection 2013 Dec 27. PMID: 24454573; PMCID: PMC3896266.
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The synthesis of multi-substituted pyrrolidinones via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes.

Organic & biomolecular chemistry

Zhang Y, Ma H, Liu X, Cui X, Wang S, Zhan Z, Pu J, Huang G.
PMID: 29855642
Org Biomol Chem. 2018 Jun 20;16(24):4439-4442. doi: 10.1039/c8ob00899j.

A novel [3 + 2] cycloaddition reaction of azaoxyallyl cations and aromatic ethylenes has been developed to afford multi-substituted pyrrolidinones in moderate to good yields. This method not only further expands the synthetic utility of α-halo hydroxamates, but also...

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Zhang Y, Ma H, Liu X, et al. The synthesis of multi-substituted pyrrolidinones via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes. Org Biomol Chem. 2018;16(24):4439-4442doi: 10.1039/c8ob00899j.
Zhang, Y., Ma, H., Liu, X., Cui, X., Wang, S., Zhan, Z., Pu, J., & Huang, G. (2018). The synthesis of multi-substituted pyrrolidinones via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes. Organic & biomolecular chemistry, 16(24), 4439-4442. https://doi.org/10.1039/c8ob00899j
Zhang, Yixin, et al. "The synthesis of multi-substituted pyrrolidinones via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes." Organic & biomolecular chemistry vol. 16,24 (2018): 4439-4442. doi: https://doi.org/10.1039/c8ob00899j
Zhang Y, Ma H, Liu X, Cui X, Wang S, Zhan Z, Pu J, Huang G. The synthesis of multi-substituted pyrrolidinones via a direct [3 + 2] cycloaddition of azaoxyallyl cations with aromatic ethylenes. Org Biomol Chem. 2018 Jun 20;16(24):4439-4442. doi: 10.1039/c8ob00899j. PMID: 29855642.
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Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones.

Organic letters

Quertenmont M, Goodall I, Lam K, Markó I, Riant O.
PMID: 32069063
Org Lett. 2020 Mar 06;22(5):1771-1775. doi: 10.1021/acs.orglett.0c00056. Epub 2020 Feb 18.

Nootropic compounds are a group of pharmacologically active pyrrolidones. These molecules, which enhance cognition properties and possess a large prescription field, are particularly interesting synthetic targets for the pharmaceutical industry. In this Article, we disclose an effective and environmentally...

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Quertenmont M, Goodall I, Lam K, et al. Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones. Org Lett. 2020;22(5):1771-1775doi: 10.1021/acs.orglett.0c00056.
Quertenmont, M., Goodall, I., Lam, K., Markó, I., & Riant, O. (2020). Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones. Organic letters, 22(5), 1771-1775. https://doi.org/10.1021/acs.orglett.0c00056
Quertenmont, Mathilde, et al. "Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones." Organic letters vol. 22,5 (2020): 1771-1775. doi: https://doi.org/10.1021/acs.orglett.0c00056
Quertenmont M, Goodall I, Lam K, Markó I, Riant O. Kolbe Anodic Decarboxylation as a Green Way To Access 2-Pyrrolidinones. Org Lett. 2020 Mar 06;22(5):1771-1775. doi: 10.1021/acs.orglett.0c00056. Epub 2020 Feb 18. PMID: 32069063.
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Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models.

Bioorganic chemistry

Žukauskas M, Grybaitė B, Jonutė P, Vaickelionienė R, Gibieža P, Vaickelionis G, Dragūnaitė B, Anusevičius K, Mickevičius V, Petrikaitė V.
PMID: 34426161
Bioorg Chem. 2021 Oct;115:105214. doi: 10.1016/j.bioorg.2021.105214. Epub 2021 Aug 09.

Synthesis of β-amino acid derivatives containing hydrazone and azole moieties is described. For this purpose, the appropriate hydrazide was treated with aromatic aldehydes, ketones and phenyl iso(thio)cyanates to obtain the desired outcome. The synthesized target compounds were evaluated for...

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Žukauskas M, Grybaitė B, Jonutė P, et al. Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models. Bioorg Chem. 2021;115:105214doi: 10.1016/j.bioorg.2021.105214.
Žukauskas, M., Grybaitė, B., Jonutė, P., Vaickelionienė, R., Gibieža, P., Vaickelionis, G., Dragūnaitė, B., Anusevičius, K., Mickevičius, V., & Petrikaitė, V. (2021). Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models. Bioorganic chemistry, 115105214. https://doi.org/10.1016/j.bioorg.2021.105214
Žukauskas, Mindaugas, et al. "Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models." Bioorganic chemistry vol. 115 (2021): 105214. doi: https://doi.org/10.1016/j.bioorg.2021.105214
Žukauskas M, Grybaitė B, Jonutė P, Vaickelionienė R, Gibieža P, Vaickelionis G, Dragūnaitė B, Anusevičius K, Mickevičius V, Petrikaitė V. Evaluation of N-aryl-β-alanine derivatives as anticancer agents in triple-negative breast cancer and glioblastoma in vitro models. Bioorg Chem. 2021 Oct;115:105214. doi: 10.1016/j.bioorg.2021.105214. Epub 2021 Aug 09. PMID: 34426161.
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Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Ren X, Guo Q, Chen J, Xie H, Xu Q, Lu Z.
PMID: 27770547
Chemistry. 2016 Dec 23;22(52):18695-18699. doi: 10.1002/chem.201603977. Epub 2016 Nov 15.

The visible-light-promoted diastereodivergent intramolecular oxyamination of alkenes is described to construct oxazolindinones, pyrrolidinones and imidazolidones via mild generation of primary amidyl radicals from functionalized hydroxylamines. A unique phenomenon of highly diastereoselective ring-opening of aziridines controlled by electron sacrifices was...

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Ren X, Guo Q, Chen J, et al. Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes. Chemistry. 2016;22(52):18695-18699doi: 10.1002/chem.201603977.
Ren, X., Guo, Q., Chen, J., Xie, H., Xu, Q., & Lu, Z. (2016). Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes. Chemistry (Weinheim an der Bergstrasse, Germany), 22(52), 18695-18699. https://doi.org/10.1002/chem.201603977
Ren, Xiang, et al. "Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,52 (2016): 18695-18699. doi: https://doi.org/10.1002/chem.201603977
Ren X, Guo Q, Chen J, Xie H, Xu Q, Lu Z. Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes. Chemistry. 2016 Dec 23;22(52):18695-18699. doi: 10.1002/chem.201603977. Epub 2016 Nov 15. PMID: 27770547.
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Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S.

Organic & biomolecular chemistry

Wang CC, Zhou J, Ma ZW, Chen XP, Chen YJ.
PMID: 31596301
Org Biomol Chem. 2019 Oct 23;17(41):9200-9208. doi: 10.1039/c9ob01992h.

A highly efficient domino aza-MIRC (Michael Induced Ring Closure) reaction between barbiturate-derived alkenes and N-alkoxy α-haloamides has been achieved in moderate to excellent yields. This reaction proceeds smoothly under mild conditions via a domino aza-Michael addition/intramolecular SN2 sequence, providing...

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Wang CC, Zhou J, Ma ZW, et al. Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S. Org Biomol Chem. 2019;17(41):9200-9208doi: 10.1039/c9ob01992h.
Wang, C. C., Zhou, J., Ma, Z. W., Chen, X. P., & Chen, Y. J. (2019). Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S. Organic & biomolecular chemistry, 17(41), 9200-9208. https://doi.org/10.1039/c9ob01992h
Wang, Chuan-Chuan, et al. "Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S." Organic & biomolecular chemistry vol. 17,41 (2019): 9200-9208. doi: https://doi.org/10.1039/c9ob01992h
Wang CC, Zhou J, Ma ZW, Chen XP, Chen YJ. Synthesis of spirobarbiturate-pyrrolidinones via a domino aza-Michael/S. Org Biomol Chem. 2019 Oct 23;17(41):9200-9208. doi: 10.1039/c9ob01992h. PMID: 31596301.
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Transition-Metal-Free Deconstructive Lactamization of Piperidines.

Angewandte Chemie (International ed. in English)

Romero-Ibañez J, Cruz-Gregorio S, Sandoval-Lira J, Hernández-Pérez JM, Quintero L, Sartillo-Piscil F.
PMID: 30998837
Angew Chem Int Ed Engl. 2019 Jun 24;58(26):8867-8871. doi: 10.1002/anie.201903880. Epub 2019 May 17.

One of the major challenges in organic synthesis is the activation or deconstructive functionalization of unreactive C(sp

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Romero-Ibañez J, Cruz-Gregorio S, Sandoval-Lira J, et al. Transition-Metal-Free Deconstructive Lactamization of Piperidines. Angew Chem Int Ed Engl. 2019;58(26):8867-8871doi: 10.1002/anie.201903880.
Romero-Ibañez, J., Cruz-Gregorio, S., Sandoval-Lira, J., Hernández-Pérez, J. M., Quintero, L., & Sartillo-Piscil, F. (2019). Transition-Metal-Free Deconstructive Lactamization of Piperidines. Angewandte Chemie (International ed. in English), 58(26), 8867-8871. https://doi.org/10.1002/anie.201903880
Romero-Ibañez, Julio, et al. "Transition-Metal-Free Deconstructive Lactamization of Piperidines." Angewandte Chemie (International ed. in English) vol. 58,26 (2019): 8867-8871. doi: https://doi.org/10.1002/anie.201903880
Romero-Ibañez J, Cruz-Gregorio S, Sandoval-Lira J, Hernández-Pérez JM, Quintero L, Sartillo-Piscil F. Transition-Metal-Free Deconstructive Lactamization of Piperidines. Angew Chem Int Ed Engl. 2019 Jun 24;58(26):8867-8871. doi: 10.1002/anie.201903880. Epub 2019 May 17. PMID: 30998837.
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Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides.

Organic letters

Xu YW, Hu XP.
PMID: 31553196
Org Lett. 2019 Oct 04;21(19):8091-8096. doi: 10.1021/acs.orglett.9b03081. Epub 2019 Sep 25.

A copper-catalyzed regio-, diastereo-, and enantioselective decarboxylative ring-opening [3 + 2] annulation of tertiary propargylic carbamates with γ-butenolides for the synthesis of optically active pyrrolidinones has been realized. The reaction proceeded through regioselective α-attack of γ-butenolide and generated highly...

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Xu YW, Hu XP. Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides. Org Lett. 2019;21(19):8091-8096doi: 10.1021/acs.orglett.9b03081.
Xu, Y. W., & Hu, X. P. (2019). Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides. Organic letters, 21(19), 8091-8096. https://doi.org/10.1021/acs.orglett.9b03081
Xu, You-Wei, and Hu, Xiang-Ping. "Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides." Organic letters vol. 21,19 (2019): 8091-8096. doi: https://doi.org/10.1021/acs.orglett.9b03081
Xu YW, Hu XP. Diastereo- and Enantioselective Copper-Catalyzed Decarboxylative Ring-Opening [3 + 2] Annulation of Tertiary Propargylic Carbamates through Regioselective α-Attack of γ-Butenolides. Org Lett. 2019 Oct 04;21(19):8091-8096. doi: 10.1021/acs.orglett.9b03081. Epub 2019 Sep 25. PMID: 31553196.
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Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines.

Chemical communications (Cambridge, England)

Ametovski J, Dutta U, Burchill L, Maiti D, Lupton DW, Hooper JF.
PMID: 29165450
Chem Commun (Camb). 2017 Dec 05;53(97):13071-13074. doi: 10.1039/c7cc08252e.

The (5 + 1) annulation of ynone/cinnamates and related substrates with protected primary amines gives rise to isoquinolones, pyrrolidinones and pyrrolopiperazines in good to excellent yields under phosphine catalysis. The reaction is viable with chiral phosphines, although the selectivity...

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Ametovski J, Dutta U, Burchill L, et al. Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines. Chem Commun (Camb). 2017;53(97):13071-13074doi: 10.1039/c7cc08252e.
Ametovski, J., Dutta, U., Burchill, L., Maiti, D., Lupton, D. W., & Hooper, J. F. (2017). Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines. Chemical communications (Cambridge, England), 53(97), 13071-13074. https://doi.org/10.1039/c7cc08252e
Ametovski, Jhi, et al. "Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines." Chemical communications (Cambridge, England) vol. 53,97 (2017): 13071-13074. doi: https://doi.org/10.1039/c7cc08252e
Ametovski J, Dutta U, Burchill L, Maiti D, Lupton DW, Hooper JF. Phosphine catalysed (5 + 1) annulation of ynone/cinnamates with primary amines. Chem Commun (Camb). 2017 Dec 05;53(97):13071-13074. doi: 10.1039/c7cc08252e. PMID: 29165450.
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Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration.

Chemistry (Weinheim an der Bergstrasse, Germany)

Yeom HS, So E, Shin S.
PMID: 21274923
Chemistry. 2011 Feb 07;17(6):1764-7. doi: 10.1002/chem.201002863. Epub 2011 Jan 05.

No abstract available.

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Yeom HS, So E, Shin S. Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration. Chemistry. 2011;17(6):1764-7doi: 10.1002/chem.201002863.
Yeom, H. S., So, E., & Shin, S. (2011). Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration. Chemistry (Weinheim an der Bergstrasse, Germany), 17(6), 1764-7. https://doi.org/10.1002/chem.201002863
Yeom, Hyun-Suk, et al. "Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 17,6 (2011): 1764-7. doi: https://doi.org/10.1002/chem.201002863
Yeom HS, So E, Shin S. Gold-catalyzed synthesis of 3-pyrrolidinones and nitrones from N-sulfonyl hydroxylamines via oxygen-transfer redox and 1,3-sulfonyl migration. Chemistry. 2011 Feb 07;17(6):1764-7. doi: 10.1002/chem.201002863. Epub 2011 Jan 05. PMID: 21274923.
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Showing 1 to 12 of 45 entries