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Nickel-catalysed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes.

Chemical communications (Cambridge, England)

Inami T, Kurahashi T, Matsubara S.
PMID: 25477001
Chem Commun (Camb). 2015 Jan 25;51(7):1285-8. doi: 10.1039/c4cc09123j.

The thiocarbamoylation of internal alkynes to produce tetrasubstituted β-aminocarbonyl vinyl sulfides was demonstrated using a nickel catalyst. This reaction was successful with a wide variety of substituents, and gave the syn-adducts exclusively.

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Inami T, Kurahashi T, Matsubara S. Nickel-catalysed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes. Chem Commun (Camb). 2015;51(7):1285-8doi: 10.1039/c4cc09123j.
Inami, T., Kurahashi, T., & Matsubara, S. (2015). Nickel-catalysed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes. Chemical communications (Cambridge, England), 51(7), 1285-8. https://doi.org/10.1039/c4cc09123j
Inami, Tasuku, et al. "Nickel-catalysed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes." Chemical communications (Cambridge, England) vol. 51,7 (2015): 1285-8. doi: https://doi.org/10.1039/c4cc09123j
Inami T, Kurahashi T, Matsubara S. Nickel-catalysed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes. Chem Commun (Camb). 2015 Jan 25;51(7):1285-8. doi: 10.1039/c4cc09123j. PMID: 25477001.
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Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates.

Organic letters

Mampuys P, Zhu Y, Sergeyev S, Ruijter E, Orru RV, Van Doorslaer S, Maes BU.
PMID: 27276236
Org Lett. 2016 Jun 17;18(12):2808-11. doi: 10.1021/acs.orglett.6b01023. Epub 2016 Jun 08.

A new method for the synthesis of secondary thiocarbamates from readily available isocyanides and thiosulfonates with broad functional group tolerance is reported. The reaction proceeds under mild reaction conditions in isopropanol and is catalyzed by inexpensive sodium iodide.

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Mampuys P, Zhu Y, Sergeyev S, et al. Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates. Org Lett. 2016;18(12):2808-11doi: 10.1021/acs.orglett.6b01023.
Mampuys, P., Zhu, Y., Sergeyev, S., Ruijter, E., Orru, R. V., Van Doorslaer, S., & Maes, B. U. (2016). Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates. Organic letters, 18(12), 2808-11. https://doi.org/10.1021/acs.orglett.6b01023
Mampuys, Pieter, et al. "Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates." Organic letters vol. 18,12 (2016): 2808-11. doi: https://doi.org/10.1021/acs.orglett.6b01023
Mampuys P, Zhu Y, Sergeyev S, Ruijter E, Orru RV, Van Doorslaer S, Maes BU. Iodide-Catalyzed Synthesis of Secondary Thiocarbamates from Isocyanides and Thiosulfonates. Org Lett. 2016 Jun 17;18(12):2808-11. doi: 10.1021/acs.orglett.6b01023. Epub 2016 Jun 08. PMID: 27276236.
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Radical cyclization by ipso substitution of the methoxy group: considerable effect of HMPA on samarium-mediated cyclization.

The Journal of organic chemistry

Ohno H, Wakayama R, Maeda S, Iwasaki H, Okumura M, Iwata C, Mikamiyama H, Tanaka T.
PMID: 12868925
J Org Chem. 2003 Jul 25;68(15):5909-16. doi: 10.1021/jo0343174.

Alkyl radicals generated by treatment of thiocarbamates of conformationally favorable 3-alkyl-3-arylpropan-1-ols with tris(trimethylsilyl)silane and AIBN efficiently undergo intramolecular ipso substitution of the methoxy group, yielding the corresponding cyclized products. In contrast, either conformationally favorable or flexible 1-arylalkan-3- or 4-ones...

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Ohno H, Wakayama R, Maeda S, et al. Radical cyclization by ipso substitution of the methoxy group: considerable effect of HMPA on samarium-mediated cyclization. J Org Chem. 2003;68(15):5909-16doi: 10.1021/jo0343174.
Ohno, H., Wakayama, R., Maeda, S., Iwasaki, H., Okumura, M., Iwata, C., Mikamiyama, H., & Tanaka, T. (2003). Radical cyclization by ipso substitution of the methoxy group: considerable effect of HMPA on samarium-mediated cyclization. The Journal of organic chemistry, 68(15), 5909-16. https://doi.org/10.1021/jo0343174
Ohno, Hiroaki, et al. "Radical cyclization by ipso substitution of the methoxy group: considerable effect of HMPA on samarium-mediated cyclization." The Journal of organic chemistry vol. 68,15 (2003): 5909-16. doi: https://doi.org/10.1021/jo0343174
Ohno H, Wakayama R, Maeda S, Iwasaki H, Okumura M, Iwata C, Mikamiyama H, Tanaka T. Radical cyclization by ipso substitution of the methoxy group: considerable effect of HMPA on samarium-mediated cyclization. J Org Chem. 2003 Jul 25;68(15):5909-16. doi: 10.1021/jo0343174. PMID: 12868925.
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A fully automated LC/MS method development and quantification protocol targeting 52 carbamates, thiocarbamates, and phenylureas.

Analytical chemistry

Yu K, Krol J, Balogh M, Monks I.
PMID: 14632123
Anal Chem. 2003 Aug 15;75(16):4103-12. doi: 10.1021/ac034044c.

We have developed a fully automated LC/MS method development and quantification protocol targeting 52 carbamtes, thiocarbamates, and phenylureas. This is a simple LC/MS method with direct injection; no post-column derivatization was required. The method utilized the Waters Alliance HT...

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Yu K, Krol J, Balogh M, et al. A fully automated LC/MS method development and quantification protocol targeting 52 carbamates, thiocarbamates, and phenylureas. Anal Chem. 2003;75(16):4103-12doi: 10.1021/ac034044c.
Yu, K., Krol, J., Balogh, M., & Monks, I. (2003). A fully automated LC/MS method development and quantification protocol targeting 52 carbamates, thiocarbamates, and phenylureas. Analytical chemistry, 75(16), 4103-12. https://doi.org/10.1021/ac034044c
Yu, Kate, et al. "A fully automated LC/MS method development and quantification protocol targeting 52 carbamates, thiocarbamates, and phenylureas." Analytical chemistry vol. 75,16 (2003): 4103-12. doi: https://doi.org/10.1021/ac034044c
Yu K, Krol J, Balogh M, Monks I. A fully automated LC/MS method development and quantification protocol targeting 52 carbamates, thiocarbamates, and phenylureas. Anal Chem. 2003 Aug 15;75(16):4103-12. doi: 10.1021/ac034044c. PMID: 14632123.
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A facile method for the synthesis of thiocarbamates: palladium-catalyzed reaction of disulfide, amine, and carbon monoxide.

The Journal of organic chemistry

Nishiyama Y, Kawamatsu H, Sonoda N.
PMID: 15787542
J Org Chem. 2005 Apr 01;70(7):2551-4. doi: 10.1021/jo048350h.

[reaction: see text] A new method for the synthesis of thiocarbamates has been developed. When dialkyl or diaryl disulfides were allowed to react with secondary amines and carbon monoxide in the presence of a catalytic amount of a palladium...

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Nishiyama Y, Kawamatsu H, Sonoda N. A facile method for the synthesis of thiocarbamates: palladium-catalyzed reaction of disulfide, amine, and carbon monoxide. J Org Chem. 2005;70(7):2551-4doi: 10.1021/jo048350h.
Nishiyama, Y., Kawamatsu, H., & Sonoda, N. (2005). A facile method for the synthesis of thiocarbamates: palladium-catalyzed reaction of disulfide, amine, and carbon monoxide. The Journal of organic chemistry, 70(7), 2551-4. https://doi.org/10.1021/jo048350h
Nishiyama, Yutaka, et al. "A facile method for the synthesis of thiocarbamates: palladium-catalyzed reaction of disulfide, amine, and carbon monoxide." The Journal of organic chemistry vol. 70,7 (2005): 2551-4. doi: https://doi.org/10.1021/jo048350h
Nishiyama Y, Kawamatsu H, Sonoda N. A facile method for the synthesis of thiocarbamates: palladium-catalyzed reaction of disulfide, amine, and carbon monoxide. J Org Chem. 2005 Apr 01;70(7):2551-4. doi: 10.1021/jo048350h. PMID: 15787542.
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Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis.

The Journal of organic chemistry

Klásek A, Mrkvicka V, Pevec A, Kosmrlj J.
PMID: 15307735
J Org Chem. 2004 Aug 20;69(17):5646-51. doi: 10.1021/jo0493370.

Novel tandem hydration of alpha-thiocyanatoketones to thiocarbamates followed by in situ cyclodehydration to fused 2-oxo-3-thiazolines is described. The reaction is applied to the synthesis of [1,3]thiazolo[5,4-c]quinoline-2,4(3aH,5H)-diones (4). Concentrated sulfuric acid was found to be critical for the reaction as...

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Klásek A, Mrkvicka V, Pevec A, et al. Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. J Org Chem. 2004;69(17):5646-51doi: 10.1021/jo0493370.
Klásek, A., Mrkvicka, V., Pevec, A., & Kosmrlj, J. (2004). Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. The Journal of organic chemistry, 69(17), 5646-51. https://doi.org/10.1021/jo0493370
Klásek, Antonín, et al. "Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis." The Journal of organic chemistry vol. 69,17 (2004): 5646-51. doi: https://doi.org/10.1021/jo0493370
Klásek A, Mrkvicka V, Pevec A, Kosmrlj J. Novel tandem hydration/cyclodehydration of alpha-thiocyanatoketones to 2-oxo-3-thiazolines. Application to thiazolo[5,4-c]quinoline-2,4(3aH,5H)-dione synthesis. J Org Chem. 2004 Aug 20;69(17):5646-51. doi: 10.1021/jo0493370. PMID: 15307735.
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Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones.

ACS omega

Pal A, Hussaini SR.
PMID: 31459329
ACS Omega. 2019 Jan 04;4(1):269-280. doi: 10.1021/acsomega.8b02633. eCollection 2019 Jan 31.

The coupling of thioamides and donor/acceptor-substituted diazocarbonyl compounds is reported for the first time. The present report provides a mild, catalytic method that couples thioamides and donor/acceptor-substituted diazocarbonyl compounds to form enamino esters and enaminones. Unlike traditional methods for...

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Pal A, Hussaini SR. Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones. ACS Omega. 2019;4(1):269-280doi: 10.1021/acsomega.8b02633.
Pal, A., & Hussaini, S. R. (2019). Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones. ACS omega, 4(1), 269-280. https://doi.org/10.1021/acsomega.8b02633
Pal, Arpan, and Hussaini, Syed Raziullah. "Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones." ACS omega vol. 4,1 (2019): 269-280. doi: https://doi.org/10.1021/acsomega.8b02633
Pal A, Hussaini SR. Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones. ACS Omega. 2019 Jan 04;4(1):269-280. doi: 10.1021/acsomega.8b02633. eCollection 2019 Jan 31. PMID: 31459329; PMCID: PMC6648369.
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Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates.

Organic & biomolecular chemistry

Pathare RS, Patil V, Kaur H, Maurya AK, Agnihotri VK, Khan S, Devunuri N, Sharon A, Sawant DM.
PMID: 30206628
Org Biomol Chem. 2018 Sep 26;16(37):8263-8266. doi: 10.1039/c8ob01855c.

A novel and efficient metal free, redox-neutral method for the synthesis of secondary thiocarbamates by cross-coupling of readily available thiophenol and isocyanides has been developed. The present methodology exhibits a broad substrate scope with good to excellent yields without...

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Pathare RS, Patil V, Kaur H, et al. Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates. Org Biomol Chem. 2018;16(37):8263-8266doi: 10.1039/c8ob01855c.
Pathare, R. S., Patil, V., Kaur, H., Maurya, A. K., Agnihotri, V. K., Khan, S., Devunuri, N., Sharon, A., & Sawant, D. M. (2018). Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates. Organic & biomolecular chemistry, 16(37), 8263-8266. https://doi.org/10.1039/c8ob01855c
Pathare, Ramdas S, et al. "Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates." Organic & biomolecular chemistry vol. 16,37 (2018): 8263-8266. doi: https://doi.org/10.1039/c8ob01855c
Pathare RS, Patil V, Kaur H, Maurya AK, Agnihotri VK, Khan S, Devunuri N, Sharon A, Sawant DM. Iodine-catalyzed cross-coupling of isocyanides and thiols for the synthesis of S-thiocarbamates. Org Biomol Chem. 2018 Sep 26;16(37):8263-8266. doi: 10.1039/c8ob01855c. PMID: 30206628.
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Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds.

Tetrahedron, asymmetry

Guang J, Zhao CG.
PMID: 21921975
Tetrahedron Asymmetry. 2011 Jun 15;22(11):1205-1211. doi: 10.1016/j.tetasy.2011.06.028.

The organocatalytic enantioselective tandem aldol-cyclization reactions of α-isothiocyanato imides and activated carbonyl compounds, such as isatins, an α-ketolactone and a 1,2-dione, have been studied with cinchona alkaloid-derived thiourea-catalysts. This methodology provided an easy way to access enantiomerically enriched spirobicyclic...

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Guang J, Zhao CG. Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds. Tetrahedron Asymmetry. 2011;22(11):1205-1211doi: 10.1016/j.tetasy.2011.06.028.
Guang, J., & Zhao, C. G. (2011). Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds. Tetrahedron, asymmetry, 22(11), 1205-1211. https://doi.org/10.1016/j.tetasy.2011.06.028
Guang, Jie, and Zhao, Cong-Gui. "Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds." Tetrahedron, asymmetry vol. 22,11 (2011): 1205-1211. doi: https://doi.org/10.1016/j.tetasy.2011.06.028
Guang J, Zhao CG. Organocatalytic enantioselective tandem aldol-cyclization reaction of α-isothiocyanato imides and activated carbonyl compounds. Tetrahedron Asymmetry. 2011 Jun 15;22(11):1205-1211. doi: 10.1016/j.tetasy.2011.06.028. PMID: 21921975; PMCID: PMC3171191.
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Synthesis of Secondary Amides from Thiocarbamates.

Organic letters

Mampuys P, Ruijter E, Orru RVA, Maes BUW.
PMID: 29975068
Org Lett. 2018 Jul 20;20(14):4235-4239. doi: 10.1021/acs.orglett.8b01654. Epub 2018 Jul 05.

The synthesis of secondary amides from readily accessible and bench-stable substituted S-phenyl thiocarbamates and Grignard reactants is reported. Oxidative workup allows recycling of the thiolate leaving group as diphenyl disulfide. Diphenyl disulfide can be transformed into S-phenyl benzenethiosulfonate, a...

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Mampuys P, Ruijter E, Orru RVA, et al. Synthesis of Secondary Amides from Thiocarbamates. Org Lett. 2018;20(14):4235-4239doi: 10.1021/acs.orglett.8b01654.
Mampuys, P., Ruijter, E., Orru, R. V. A., & Maes, B. U. W. (2018). Synthesis of Secondary Amides from Thiocarbamates. Organic letters, 20(14), 4235-4239. https://doi.org/10.1021/acs.orglett.8b01654
Mampuys, Pieter, et al. "Synthesis of Secondary Amides from Thiocarbamates." Organic letters vol. 20,14 (2018): 4235-4239. doi: https://doi.org/10.1021/acs.orglett.8b01654
Mampuys P, Ruijter E, Orru RVA, Maes BUW. Synthesis of Secondary Amides from Thiocarbamates. Org Lett. 2018 Jul 20;20(14):4235-4239. doi: 10.1021/acs.orglett.8b01654. Epub 2018 Jul 05. PMID: 29975068.
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Enantioselective Total Syntheses of Lyconadins A-E through a Palladium-Catalyzed Heck-Type Reaction.

Angewandte Chemie (International ed. in English)

Zhang J, Yan Y, Hu R, Li T, Bai WJ, Yang Y.
PMID: 31743549
Angew Chem Int Ed Engl. 2020 Feb 10;59(7):2860-2866. doi: 10.1002/anie.201912948. Epub 2020 Jan 07.

A novel palladium-catalyzed Heck-type reaction of thiocarbamates has been designed to construct bridged seven-membered-ring systems that are otherwise challenging to prepare. Taking advantage of this newly developed method, enantioselective syntheses of lyconadins A-E (1-5), lycopecurine (6), and dehydrolycopecurine (7)...

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Zhang J, Yan Y, Hu R, et al. Enantioselective Total Syntheses of Lyconadins A-E through a Palladium-Catalyzed Heck-Type Reaction. Angew Chem Int Ed Engl. 2020;59(7):2860-2866doi: 10.1002/anie.201912948.
Zhang, J., Yan, Y., Hu, R., Li, T., Bai, W. J., & Yang, Y. (2020). Enantioselective Total Syntheses of Lyconadins A-E through a Palladium-Catalyzed Heck-Type Reaction. Angewandte Chemie (International ed. in English), 59(7), 2860-2866. https://doi.org/10.1002/anie.201912948
Zhang, Jiayang, et al. "Enantioselective Total Syntheses of Lyconadins A-E through a Palladium-Catalyzed Heck-Type Reaction." Angewandte Chemie (International ed. in English) vol. 59,7 (2020): 2860-2866. doi: https://doi.org/10.1002/anie.201912948
Zhang J, Yan Y, Hu R, Li T, Bai WJ, Yang Y. Enantioselective Total Syntheses of Lyconadins A-E through a Palladium-Catalyzed Heck-Type Reaction. Angew Chem Int Ed Engl. 2020 Feb 10;59(7):2860-2866. doi: 10.1002/anie.201912948. Epub 2020 Jan 07. PMID: 31743549.
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Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process.

Chemical communications (Cambridge, England)

Zhou L, Tay DW, Chen J, Leung GY, Yeung YY.
PMID: 23072774
Chem Commun (Camb). 2013 May 14;49(39):4412-4. doi: 10.1039/c2cc36578b. Epub 2012 Oct 16.

A catalytic enantioselective bromocyclization of olefinic amides using amino-thiocarbamates as the catalysts has been developed. The resulting enantioenriched 2-substituted 3-bromopiperidines can readily be transformed to 3-substituted piperidines through a silver salt-mediated rearrangement. This process has been applied to the...

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Zhou L, Tay DW, Chen J, et al. Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process. Chem Commun (Camb). 2012;49(39):4412-4doi: 10.1039/c2cc36578b.
Zhou, L., Tay, D. W., Chen, J., Leung, G. Y., & Yeung, Y. Y. (2013). Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process. Chemical communications (Cambridge, England), 49(39), 4412-4. https://doi.org/10.1039/c2cc36578b
Zhou, Ling, et al. "Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process." Chemical communications (Cambridge, England) vol. 49,39 (2013): 4412-4. doi: https://doi.org/10.1039/c2cc36578b
Zhou L, Tay DW, Chen J, Leung GY, Yeung YY. Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process. Chem Commun (Camb). 2013 May 14;49(39):4412-4. doi: 10.1039/c2cc36578b. Epub 2012 Oct 16. PMID: 23072774.
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