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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 5
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Original Articles

4-Methoxybenzyl (PMB), A Versatile Protecting Group for the Regiospecific Lithiation and Functionalization of Pyrazoles

Chakrapani Subramanyam Department of Medicinal Chemistry, Sterling Winthrop Pharmaceutical Research Division, 1250, South Collegeville Road, Collegeville, Pennsylvania, 19426; Department of Chemistry, Cephalon, Inc., 145 Brandywine Ave, West Chester, PA, 19380-4245
Pages 761-774 | Received 15 Sep 1994, Published online: 23 Sep 2006

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Anusuya Choudhury, Michael E. Pierce & Pat N. Confalone. (2001) OXIDATIVE REMOVAL OF p-METH-OXYBENZYL-AMINO PROTECTING GROUP IN THE PRESENCE OF A PROXIMAL HYDROXY FUNCTION: A SOLUTION TO A PROCESS PROBLEM IN SUSTIVA® (EFAVIRENZ) SYNTHESIS. Synthetic Communications 31:23, pages 3707-3714.
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Articles from other publishers (27)

Clément Jacob & Clemens Lamberth. (2019) First synthesis and further derivatization of furo[3,2-c]pyrazol-6-ones. Tetrahedron Letters 60:7, pages 530-533.
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Nicola Luise & Paul G. Wyatt. (2018) Generation of Polar Semi-Saturated Bicyclic Pyrazoles for Fragment-Based Drug-Discovery Campaigns.. Chemistry - A European Journal 24:41, pages 10443-10451.
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Martin Pisár, Eva Schütznerová, Filip Hančík, Igor Popa, Zdeněk Trávníček & Petr Cankař. (2018) Modification of Boc-Protected CAN508 via Acylation and Suzuki-Miyaura Coupling. Molecules 23:1, pages 149.
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Bachir Latli, Matt Hrapchak, Joe J. Gao, Carl A. Busacca & Chris H. Senanayake. (2015) A novel five-lipoxygenase activity protein inhibitor labeled with carbon-14 and deuterium. Journal of Labelled Compounds and Radiopharmaceuticals 58:9, pages 390-394.
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Seri Bae, Ha-Lim Jang, Haeun Jung & Jung Min Joo. (2014) Catalytic C–H Allylation and Benzylation of Pyrazoles. The Journal of Organic Chemistry 80:1, pages 690-697.
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Basil M. Ahmed & Gellert Mezei. (2015) Green protection of pyrazole, thermal isomerization and deprotection of tetrahydropyranylpyrazoles, and high-yield, one-pot synthesis of 3(5)-alkylpyrazoles. RSC Advances 5:31, pages 24081-24093.
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. 2014. Greene's Protective Groups in Organic Synthesis. Greene's Protective Groups in Organic Synthesis 895 1193 .
George Agelis, Amalia Resvani, Catherine Koukoulitsa, Tereza Tůmová, Jiřina Slaninová, Dimitra Kalavrizioti, Katerina Spyridaki, Antreas Afantitis, Georgia Melagraki, Athanasia Siafaka, Eleni Gkini, Grigorios Megariotis, Simona Golic Grdadolnik, Manthos G. Papadopoulos, Demetrios Vlahakos, Michael Maragoudakis, George Liapakis, Thomas Mavromoustakos & John Matsoukas. (2013) Rational design, efficient syntheses and biological evaluation of N , N ′-symmetrically bis-substituted butylimidazole analogs as a new class of potent Angiotensin II receptor blockers. European Journal of Medicinal Chemistry 62, pages 352-370.
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Christina Despotopoulou, Lydia Klier & Paul Knochel. (2009) Synthesis of Fully Substituted Pyrazoles via Regio- and Chemoselective Metalations. Organic Letters 11:15, pages 3326-3329.
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Jun Pu, Anthony F. Kreft, Suzan H. Aschmies, Kevin P. Atchison, Joshua Berkowitz, Thomas J. Caggiano, Micheal Chlenov, George Diamantidis, Boyd L. Harrison, Yun Hu, Donna Huryn, J. Steven Jacobsen, Mei Jin, Kerri Lipinski, Peimin Lu, Robert L. Martone, Koi Morris, June Sonnenberg-Reines, Dave R. Riddell, Joan Sabalski, Shaiu-Ching Sun, Erik Wagner, Yiqun Wang, Zheng Xu, Hua Zhou & Lynn Resnick. (2009) Synthesis and structure–activity relationship of a novel series of heterocyclic sulfonamide γ-secretase inhibitors. Bioorganic & Medicinal Chemistry 17:13, pages 4708-4717.
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Takeshi Hanamoto, Eri Hashimoto, Masayuki Miura, Hiroshi Furuno & Junji Inanaga. (2008) Reaction of N -Methyl-5-tributylstannyl-4-fluoro-1 H -pyrazole and Its Application to N -Methyl-chromeno[2,3- d ]pyrazol-9-one Synthesis . The Journal of Organic Chemistry 73:12, pages 4736-4739.
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Manolis A. Fousteris, Athanasios Papakyriakou, Anna Koutsourea, Maria Manioudaki, Evgenia Lampropoulou, Evangelia Papadimitriou, Georgios A. Spyroulias & Sotiris S. Nikolaropoulos. (2008) Pyrrolo[2,3- a ]carbazoles as Potential Cyclin Dependent Kinase 1 (CDK1) Inhibitors. Synthesis, Biological Evaluation, and Binding Mode through Docking Simulations . Journal of Medicinal Chemistry 51:4, pages 1048-1052.
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Barry M. Trost, Nicolai Cramer & Heiko Bernsmann. (2007) Concise Total Synthesis of (±)-Marcfortine B. Journal of the American Chemical Society 129:11, pages 3086-3087.
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Wolfgang Holzer, Gernot A. Eller, Andreas W. Haring, Barbara Datterl & Maryam Zwettler. (2007) Tri- and Tetracyclic Heteroaromatic Systems: Synthesis of Novel Benzo-, Benzothieno- and Thieno-Fused Pyrano[2,3-c]pyrazol-4(1H)-ones. HETEROCYCLES 71:1, pages 87.
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Marc Lamblin, Axel Couture, Eric Deniau & Pierre Grandclaudon. (2007) A concise first total synthesis of narceine imide. Organic & Biomolecular Chemistry 5:9, pages 1466.
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Brian Iddon, Janne Ejrnæs Tønder, Masood Hosseini & Mikael Begtrup. (2007) The N-vinyl group as a protection group of the preparation of 3(5)-substituted pyrazoles via bromine–lithium exchange. Tetrahedron 63:1, pages 56-61.
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Takeshi Hanamoto, Mikio Egashira, Kentaro Ishizuka, Hiroshi Furuno & Junji Inanaga. (2006) Synthesis and reactions of 1-methyl-5-tributylstannyl-4-trifluoromethylpyrazole. Tetrahedron 62:26, pages 6332-6338.
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Levente Ondi & Manfred Schlosser. (2006) Metalated 1-(p-Methoxybenzyl)pyrazole: A Structural Chameleon. European Journal of Organic Chemistry 2006:10, pages 2417-2422.
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Marc Lamblin, Axel Couture, Eric Deniau & Pierre Grandclaudon. (2006) A brief total synthesis of fumaramidine. Tetrahedron 62:12, pages 2917-2921.
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Wolfgang Holzer & Gernot A. Eller. (2004) The 4-Methoxybenzyl (PMB) Function as a Versatile Protecting Group in the Synthesis of N-Unsubstituted Pyrazolones. HETEROCYCLES 63:11, pages 2537.
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Kateřina Černovská, Miriam Kemter, Hans-Christoph Gallmeier, Petra Rzepecki, Thomas Schrader & Burkhard König. (2004) PEG-supported synthesis of pyrazole oligoamides with peptide β-sheet affinity. Org. Biomol. Chem. 2:11, pages 1603-1611.
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Jørgen Eskildsen, Jesper Kristensen, Per Vedsø & Mikael Begtrup. (2001) Convergent Synthesis of 3-Arylated 1-Hydroxypyrazoles via 3-Metalated Pyrazole-1-oxides. The Journal of Organic Chemistry 66:25, pages 8654-8656.
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Axel Couture, Eric Deniau, Pierre Grandclaudon & Christophe Hoarau. (1998) Total Syntheses of Taliscanine, Velutinam, and Enterocarpam II. The Journal of Organic Chemistry 63:9, pages 3128-3132.
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Nicoletta Almirante, Alberto Cerri, Giorgio Fedrizzi, Giuseppe Marazzi & Marco Santagostino. (1998) A general, [1+4] approach to the synthesis of 3(5)-substituted pyrazoles from aldehydes. Tetrahedron Letters 39:20, pages 3287-3290.
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S.A. LangJr.Jr. & V.J. Lee. 1996. 146 162 .
Chakrapani Subramanyam. (1995) An Unusual dependency of counterion during wittig methylenation of bis-heteroaryl ketones. Tetrahedron Letters 36:51, pages 9249-9252.
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C. SUBRAMANYAM. (2010) ChemInform Abstract: 4‐Methoxybenzyl (PMB), a Versatile Protecting Group for the Regiospecific Lithiation and Functionalization of Pyrazoles.. ChemInform 26:27.
Crossref

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