Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 24
Submit an article Journal homepage
1,080
Views
23
CrossRef citations to date
0
Altmetric
Original Articles

N-3-ALKYLATION OF URACIL AND DERIVATIVES VIA N-1-BOC PROTECTION

Saul Jaime-Figueroa Roche Bioscience, 3401 Hillview Ave., Palo Alto, CA, 94304, U.S.A.Correspondence[email protected]
,
Alejandro Zamilpa Roche Bioscience, 3401 Hillview Ave., Palo Alto, CA, 94304, U.S.A.
,
Angel Guzmán Roche Bioscience, 3401 Hillview Ave., Palo Alto, CA, 94304, U.S.A.
&
David J. Morgans Jr. Roche Bioscience, 3401 Hillview Ave., Palo Alto, CA, 94304, U.S.A.
Pages 3739-3746 | Received 07 Feb 2001, Published online: 09 Nov 2006

Citations (23)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (2)

Ahmed Khalil, Keisuke Ishita, Tehane Ali, Rohit Tiwari, Ramy Riachy, Antonio Toppino, Sherifa Hasabelnaby, Naum Sayfullin, Allen G. Oliver, Judith Gallucci, Zhenguo Huang & Werner Tjarks. (2014) Iodine Monochloride Facilitated Deglycosylation, Anomerization, and Isomerization of 3-Substituted Thymidine Analogues. Nucleosides, Nucleotides & Nucleic Acids 33:12, pages 786-799.
Read now
Jason Choy, Saul Jaime-Figueroa, Laurence Jiang & Paul Wagner. (2008) Novel Practical Deprotection of N-Boc Compounds Using Fluorinated Alcohols. Synthetic Communications 38:21, pages 3840-3853.
Read now

Articles from other publishers (21)

Zeyu Dai, Bin Han, Zonglin Li & Zhimin Li. (2023) Modularized reconstruction of pyrimidine pathway in Escherichia coli for enhanced pyrimidine nucleosides biosynthesis. Biochemical Engineering Journal 200, pages 109101.
Crossref
Tao Cao, Michael L. Martini, Kwang-Su Park, H. Ümit Kaniskan & Jian Jin. 2022. Comprehensive Heterocyclic Chemistry IV. Comprehensive Heterocyclic Chemistry IV 86 228 .
Djenisa H. A. Rocha, Carmen M. Machado, Vera Sousa, Cristiana F. V. Sousa, Vera L. M. Silva, Artur M. S. Silva, João Borges & João F. Mano. (2021) Customizable and Regioselective One‐Pot N−H Functionalization of DNA Nucleobases to Create a Library of Nucleobase Derivatives for Biomedical Applications. European Journal of Organic Chemistry 2021:31, pages 4423-4433.
Crossref
Ewa Mironiuk-Puchalska, Włodzimierz Buchowicz, Piotr Grześkowiak, Patrycja Wińska, Monika Wielechowska, Olena Karatsai, Maria Jolanta Rędowicz, Maria Bretner & Mariola Koszytkowska-Stawińska. (2019) Potential bioisosteres of β-uracilalanines derived from 1H-1,2,3-triazole-C-carboxylic acids. Bioorganic Chemistry 83, pages 500-510.
Crossref
Olga Michalak, Piotr Cmoch, Piotr Krzeczyński, Marcin Cybulski & Andrzej Leś. (2019) A diversity of alkylation/acylation products of uracil and its derivatives: synthesis and a structural study. Organic & Biomolecular Chemistry 17:2, pages 354-362.
Crossref
S. N. Dubovitskii, N. G. Komissarova, O. V. Shitikova, L. V. Spirikhin, M. F. Abdullin & M. S. Yunusov. (2015) Synthesis of Betulin 28-(2-Bromoacetate) Conjugates with Uracil and its Methyl-Substituted Homologs. Chemistry of Natural Compounds 51:3, pages 505-511.
Crossref
Sophie Racine, Florian de Nanteuil, Eloisa Serrano & Jérôme Waser. (2014) Synthesis of (Carbo)nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes. Angewandte Chemie International Edition 53:32, pages 8484-8487.
Crossref
Sophie Racine, Florian de Nanteuil, Eloisa Serrano & Jérôme Waser. (2014) Synthesis of (Carbo)nucleoside Analogues by [3+2] Annulation of Aminocyclopropanes. Angewandte Chemie 126:32, pages 8624-8627.
Crossref
Ali Khalaj, Khosrou Abdi, Seyed Nasser Ostad, Mohammad Reza Khoshayand, Navid Lamei & Hasan Ali Nedaie. (2014) Synthesis, In Vitro Cytotoxicity and Radiosensitizing Activity of Novel 3-[(2,4-Dinitrophenylamino)Alkyl] Derivatives of 5-Fluorouracil . Chemical Biology & Drug Design 83:2, pages 183-190.
Crossref
Khosrou Abdi, Ali Khalaj, Seyed Nasser Ostad, Navid Lamei & Mohammad Reza Khoshayand. (2013) Synthesis, in vitro aerobic and hypoxic cytotoxicity and radiosensitizing activity of novel metronidazole tethered 5-fluorouracil. DARU Journal of Pharmaceutical Sciences 21:1.
Crossref
Daniela Pizzirani, Chiara Pagliuca, Natalia Realini, Davide Branduardi, Giovanni Bottegoni, Marco Mor, Fabio Bertozzi, Rita Scarpelli, Daniele Piomelli & Tiziano Bandiera. (2013) Discovery of a New Class of Highly Potent Inhibitors of Acid Ceramidase: Synthesis and Structure–Activity Relationship (SAR). Journal of Medicinal Chemistry 56:9, pages 3518-3530.
Crossref
Khosrou Abdi, Ali Khalaj, Syeed-Naser Ostad & Mohammad Reza Khoshayand. (2012) Cytotoxicity and radiosensitising activity of synthesized dinitrophenyl derivatives of 5-fluorouracil. DARU Journal of Pharmaceutical Sciences 20:1.
Crossref
Valérie Declerck & David J. Aitken. (2011) A refined synthesis of enantiomerically pure 2-aminocyclobutanecarboxylic acids. Amino Acids 41:3, pages 587-595.
Crossref
Sławomir Boncel, Maciej Mączka & Krzysztof Z. Walczak. (2010) Michael versus retro-Michael reaction in the regioselective synthesis of N-1 and N-3 uracil adducts. Tetrahedron 66:43, pages 8450-8457.
Crossref
Joshua M. Sadler, Sylvester L. Mosley, Kathleen M. Dorgan, Zhaohui Sunny Zhou & Katherine L. Seley-Radtke. (2009) Synthetic strategies toward carbocyclic purine–pyrimidine hybrid nucleosides. Bioorganic & Medicinal Chemistry 17:15, pages 5520-5525.
Crossref
Le WANG, Yunxiao ZHANG & Jingchao TAO. (2009) Synthesis and Cytotoxicity of Derivatives of Fluorouracil Conjugated with Three‐membered Ring. Chinese Journal of Chemistry 27:7, pages 1374-1378.
Crossref
Mikkel F. Jacobsen, Martin M. Knudsen & Kurt V. Gothelf. (2006) Efficient N -Arylation and N -Alkenylation of the Five DNA/RNA Nucleobases . The Journal of Organic Chemistry 71:24, pages 9183-9190.
Crossref
Olaf R. Ludek & Chris Meier. (2006) Influence of theN3-Protection Group onN1- vs.O2-Alkylation in the Mitsunobu Reaction. European Journal of Organic Chemistry 2006:4, pages 941-946.
Crossref
Fan Wu, Musole G. Buhendwa & Donald F. Weaver. (2004) Benzhydryl as an Efficient Selective Nitrogen Protecting Group for Uracils. The Journal of Organic Chemistry 69:26, pages 9307-9309.
Crossref
F.J. Lopez, L. Arias, R. Chan, D.E. Clarke, T.R. Elworthy, A.P.D.W. Ford, A. Guzman, S. Jaime-Figueroa, J.R. Jasper, D.J. MorgansJr.Jr., F. Padilla, A. Perez-Medrano, C. Quintero, M. Romero, L. Sandoval, S.A. Smith, T.J. Williams & D.R. Blue. (2003) Synthesis, pharmacology and pharmacokinetics of 3-(4-Aryl-piperazin-1-ylalkyl)-uracils as uroselective α1A-antagonists. Bioorganic & Medicinal Chemistry Letters 13:11, pages 1873-1878.
Crossref
Saul Jaime‐Figueroa, Alejandro Zamilpa, Angel Guzman & David J. Morgans Jr.. (2010) ChemInform Abstract: N‐3‐Alkylation of Uracil and Derivatives via N‐1‐Boc Protection.. ChemInform 33:12.
Crossref

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.