Article
Chemistry, Organic
Alexander Leslie, Thomas S. Moody, Megan Smyth, Scott Wharry, Marcus Baumann
Summary: This study presented a continuous flow process that coupled a Curtius rearrangement step with a biocatalytic impurity tagging strategy to produce a series of valuable Cbz-carbamate products. Immobilized CALB was used to transform residual benzyl alcohol into benzyl butyrate, resulting in the creation of desired carbamate structures with high yield and purity. Derivatization of the products through complementary flow-based Michael addition reactions demonstrated the ability to create 13-amino acid species, highlighting the potential applicability of this work in the pharmaceutical and specialty chemical industries.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hasna Yassine, Jamila Bouali, Asmaa Oumessaoud, El Mahdi Ourhzif, Salha Hamri, Abderrafia Hafid, Mostafa Khouili, Maria Dolors Pujol
Summary: The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride can be converted into azide derivatives and ureas, leading to the synthesis of new alkyl derivatives. These new compounds were characterized by H-1 and C-13 NMR, as well as X-ray crystallographic analysis.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Tapasi Kalita, Dharm Dev, Sandip Mondal, Rajat Subhra Giri, Bhubaneswar Mandal
Summary: The direct conversion of carboxylic acids to ureas, carbamates, and thiocarbamates in a single pot via Curtius rearrangement is achieved successfully using Ethyl-2-cyano-2-(2-nitrophenylsulfonyloximino)acetate (ortho-NosylOXY, I) as a coupling reagent. This method enables the synthesis of target products with moderate to good yield and is compatible with a diverse range of N-protecting groups, while suppressing racemization generation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Song-Ning Wang, Guo-Yu Zhang, Adedamola Shoberu, Jian-Ping Zou
Summary: A new method for the preparation of carbamates using copper-catalyzed cross-coupling reaction is described, which is environmentally friendly and compatible with a wide range of amines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Camilla Loro, Julie Oble, Francesca Foschi, Marta Papis, Egle M. Beccalli, Sabrina Giofre, Giovanni Poli, Gianluigi Broggini
Summary: Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)(2) or TMSOTf as promoters results in the formation of N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the promoter and aryl substrates. A proposed mechanism explains the outcome of these C-H based cascades, involving initial acid promoted decarboxylative/deamidative Friedel-Crafts allylation followed by protonation of the allylated arene.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Dhruba P. Poudel, Richard T. Taylor
Summary: Research has shown that dendritic materials with urethane linkages are more stable than those with other functional groups, and the use of a protecting group-free onepot multicomponent Curtius reaction allows for the construction of dendritic polyurethanes with late-stage modification, resulting in surface-functionalized polyurethane dendrimers.
Article
Materials Science, Multidisciplinary
Juhyen Lee, Seohyun Baek, Hwi Hyun Moon, Seung Uk Son, Changsik Song
Summary: The study introduced a furan-based polymer platform, successfully synthesizing various polymers including photodegradable polyurethanes and heat-resistant polymers. By adjusting the polymerization conditions, the relative ratios of urethane and isocyanurate groups in the polymers could be controlled.
ACS APPLIED POLYMER MATERIALS
(2021)
Article
Chemistry, Organic
Mangal S. Yadav, Sumt K. Singh, Anand K. Agrahari, Anoop S. Singh, Vinod K. Tiwari
Summary: A diverse range of ureas, N-acylureas, carbamates, and thiocarbamates can be synthesized in good to excellent yields by reacting N-acylbenzotriazoles individually with amines or amides or phenols or thiols in the presence of diphenylphosphoryl azide (DPPA) as an azide donor. The use of DPPA as an alternative to other azide donors in Curtius degradation allows for high reaction yields under metal-free conditions with easy handling of readily available reagents.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Riyaz Ahmed, Ria Gupta, Zaheen Akhter, Mukesh Kumar, Parvinder Pal Singh
Summary: This study reports a one-pot general method using TCT as a mediator for the conversion of carboxylic acids into various functional groups. The process involves TCT-mediated acid activation, azidation, and heating, resulting in isocyanate formation via Curtius rearrangement in the presence of nucleophiles and yielding coupled products. This method shows promising potential for various applications.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Weiqiang Tan, Jifang Zheng, Le Chen, Huining Chai, Jing Guan
Summary: The efficient condensation and intramolecular cyclization of 1-hydroxyanthraquinone with various active methylene acetates mediated by Propylphosphonic anhydride (T3P) in the presence of Et3N leads to oxaperylenone derivatives. The reactive intermediate propylphosphate derivatives generated in situ from acylation of 1-hydroxyanthraquinone with T3P were confirmed. The study also proposed a plausible reaction mechanism based on density functional theory calculations. This method provides a useful approach for the synthesis of core structures of oxaperylenone derivatives.
Article
Chemistry, Multidisciplinary
Yipin Zhang, Xia Ge, Hongjian Lu, Guigen Li
Summary: Transition-metal-catalyzed sp(2) C-N bond formation is a reliable method for synthesizing aryl amines. This method introduces a cascade approach using organic carboxylic acids and easily prepared azidoformates as carbon and nitrogen sources, achieving high yields and minimal byproducts.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Christina G. Connor, Jacob C. DeForest, Phil Dietrich, Nga M. Do, Kevin M. Doyle, Shane Eisenbeis, Elizabeth Greenberg, Sarah H. Griffin, Brian P. Jones, Kris N. Jones, Michael Karmilowicz, Rajesh Kumar, Chad A. Lewis, Emma L. McInturff, J. Christopher McWilliams, Ruchi Mehta, Bao D. Nguyen, Anil M. Rane, Brian Samas, Barbara J. Sitter, Howard W. Ward, Mark E. Webster
Summary: The development of a commercial route towards the JAK1 inhibitor abrocitinib involves a late-stage Lossen rearrangement to obtain the desired compound, which is then sulfonylated using a novel water-tolerable triazole sulfonylating reagent to provide the active pharmaceutical ingredient.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Simon N. Smith, Stephen J. Connon
Summary: The ring contraction-lactamisation of anhydrides with trimethylsilylazide in the presence of an amine catalyst has been studied. It is possible to generate 5,- 6- and 8-membered ring lactams from cyclic anhydrides under controlled conditions, with a simple operation procedure. Succinic anhydrides can be used to produce N-carboxyanhydrides for polymer chemistry and as beta-peptide precursors.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Polymer Science
Azra Kocaarslan, Gorkem Yilmaz, Gokhan Topcu, Levent Demirel, Yusuf Yagci
Summary: This study demonstrates the use of a new photochemical ligation process as a versatile approach for various applications such as cross-linking polymerization, functionalization of polymer chain ends, and surface modification of different materials. The process involves the formation of urethane linkages through the reaction of photochemically in situ generated isocyanates with hydroxyl moieties. The intermediates and obtained materials were characterized using NMR, FTIR, TGA, and TEM analyses, showing the potential for future applications in fabricating complex macromolecular structures, biomaterials, and gels.
MACROMOLECULAR RAPID COMMUNICATIONS
(2021)
Article
Chemistry, Applied
Andrew Davidson, David A. Foley, Heather Frericks-Schmidt, Sally Gut Ruggeri, Madeline Herman, Shawn LaCasse, Yizhou Liu, Emma L. McInturff, Ronald Morris, Naila Mugheirbi, Brian Samas, Aritra Sarkar, Robert A. Singer, Faith Witkos, Shu Yu
Summary: Propylphosphonic anhydride, or T3P, is a commonly used reagent for amidation reactions with easy workup. This paper discusses the isolation and characterization of a T3P degradation byproduct and its removal by washing or further degradation at low pH. Another example shows the degradation of a T3P-related phosphonic ester at low pH.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Medicinal
Stefano Crosignani, Adeline Pretre, Catherine Jorand-Lebrun, Gaele Fraboulet, Jeyaprakashnarayanan Seenisamy, John Kallikat Augustine, Marc Missotten, Yves Humbert, Christophe Cleva, Nada Abla, Hamina Daff, Olivier Schott, Manfred Schneider, Fabienne Burgat-Charvillon, Delphine Rivron, Ingrid Hamernig, Jean-Francois Arrighi, Marilene Gaudet, Simone C. Zimmerli, Pierre Juillard, Zoe Johnson
JOURNAL OF MEDICINAL CHEMISTRY
(2011)
Article
Chemistry, Organic
John Kallikat Augustine, Vani Akabote, Shrivatsa Ganapati Hegde, Padma Alagarsamy
JOURNAL OF ORGANIC CHEMISTRY
(2009)
Article
Chemistry, Organic
Gwenaelle Bouscary-Desforges, Agnes Bombrun, John Kallikat Augustine, Gerald Bernardinelli, Anna Quattropani
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
Gwenaelle Bouscary-Desforges, Agnes Bombrun, John Kallikat Augustine, Gerald Bernardinelli, Anna Quattropani
JOURNAL OF ORGANIC CHEMISTRY
(2012)
Article
Chemistry, Organic
John Kallikat Augustine, Rajendra Nath Atta, Balakrishna Kolathur Ramappa, Chandrakantha Boodappa
Article
Chemistry, Organic
John Kallikat Augustine, Agnes Bombrun, Rajendra Nath Atta
Article
Chemistry, Organic
John Kallikat Augustine, Yanjerappa Arthoba Naik, Subba Poojari, Nagaraja Chowdappa, Bailur Sheena Sherigara, Kummara Areppa
SYNTHESIS-STUTTGART
(2009)
Article
Chemistry, Organic
Nagaraja Chowdappa, Bailur Sheena Sherigara, John Kallikat Augustine, Kummara Areppa, Ashis Baran Mandal
SYNTHESIS-STUTTGART
(2010)
Article
Chemistry, Organic
John Kallikat Augustine, Veeramani Vairaperumal, Sharmila Narasimhan, Padma Alagarsamy, Anbarasi Radhakrishnan
Article
Chemistry, Organic
John Kallikat Augustine, Y. Arthoba Naik, Veeramani Vairaperumal, Sharmila Narasimhan
Article
Chemistry, Organic
John Kallikat Augustine, Agnes Bombrun, Srinivasa Venkatachaliah
TETRAHEDRON LETTERS
(2011)
Article
Chemistry, Organic
John Kallikat Augustine, Agnes Bombrun, Wolfgang H. B. Sauer, Pujari Vijaykumar
TETRAHEDRON LETTERS
(2012)
Article
Chemistry, Organic
John Kallikat Augustine, Agnes Bombrun, Balakrishna Ramappa, Chandrakantha Boodappa
TETRAHEDRON LETTERS
(2012)
Article
Chemistry, Organic
John Kallikat Augustine, Agnes Bombrun, Padma Alagarsamy, Anandh Jothi
TETRAHEDRON LETTERS
(2012)
