Carbon dioxide transformation as a green alternative to phosgene and chloroformates: N-carboxyalkylation of lactams and analogues

Zhang, 2020, Catalytic transformation of CO2 into C1 chemicals using hydrosilanes as a reducing agent, Green Chem., 22, 1800, 10.1039/C9GC04342J Sahoo, 2021, CO2-promoted reactions: an emerging concept for the synthesis of fine chemicals and pharmaceuticals, ACS Catal., 11, 3414, 10.1021/acscatal.0c05681 Green, 1999 S. Chodorowski-Kimmes, P. Giustiniani, WO Pat., 2009053594A2, 2009. G. Malle, WO Pat., 2009053587A2, 2009. G. Malle, WO Pat., 2009053584A2, 2009. G. Malle, FR Pat., 2921828A1, 2009. Jaquenoud, 1961, Synthèse de la Ileu8‐oxytocine et de la Val8‐oxytocine, deux analogues de l’oxytocine modifiés dans la chaîne latérale, Helv. Chim. Acta, 44, 113, 10.1002/hlca.19610440116 A substructure search for chloroformates on retailers’ websites gave 75 references for Merck (previously Sigma-Aldrich), 53 references for Fluorochem and 21 references for TCI. Cauliez, 1991, Studies on pyrrolidones. Convenient syntheses of methyl, methyl N‐methyl‐ and methyl N‐methoxymethylpyroglutamate, J. Heterocycl. Chem., 28, 1143, 10.1002/jhet.5570280452 Rigo, 1996, Studies on pyrrolidinones. Synthesis of N‐(2‐nitrobenzyl)pyroglutamic acid, J. Heterocycl. Chem., 33, 1063, 10.1002/jhet.5570330411 Rigo, 1997, Synlett, 998, 10.1055/s-1997-944 Baudelet, 2016, Impact of functional groups on the copper-initiated N-arylation of 5-functionalized pyrrolidin-2-ones and their vinylogues, Synthesis, 48, 2226, 10.1055/s-0035-1561415 Homerin, 2016, ZrCl4 as a new catalyst for ester amidation: an efficient synthesis of h-P2X7R antagonists, Tetrahedron Lett., 57, 1165, 10.1016/j.tetlet.2016.02.004 Homerin, 2017, Discovery of highly functionalized scaffolds: pyrroloimidazolediones as P2X7 receptor antagonists, Tetrahedron, 73, 5327, 10.1016/j.tet.2017.07.036 Homerin, 2017, On the discovery of new potent human farnesyltransferase inhibitors: emerging pyroglutamic derivatives, Org. Biomol. Chem., 15, 8110, 10.1039/C7OB01489A Homerin, 2020, Pyroglutamide-based P2X7 receptor antagonists targeting inflammatory bowel disease, J. Med. Chem., 63, 2074, 10.1021/acs.jmedchem.9b00584 Katritzky, 1987, Carbon dioxide: a reagent for the simultaneous protection of nucleophilic centres and the activation of alternative locations to electrophilic attack: Part 81. a novel synthetic route to 4-substituted-2-pyridones, Tetrahedron, 43, 2343, 10.1016/S0040-4020(01)86820-4 Lihs, 2002, Kinetics and mechanism for CO2 scrambling in a N-Carboxyimidazolidone analogue for N1-Carboxybiotin, J. Am. Chem. Soc., 124, 11334, 10.1021/ja026753y Casadei, 1997, Electrogenerated superoxide-activated carbon dioxide. A new mild and safe approach to organic carbamates, J. Org. Chem., 62, 6754, 10.1021/jo970308h Chen, 2009, A novel synthesis of 1,3-oxazine-2,4-diones via a simple and efficient reaction of CO2 with 2,3-allenamides, Org. Lett., 11, 2900, 10.1021/ol9009046 Evans, 2001, Organolanthanide-based coordination and insertion reactivity of the anion formed by deprotonation of ε-caprolactam, Organometallics, 20, 4529, 10.1021/om010403n Casadei, 1995, Electrochemical studies on haloamides. Part XII. Electrosynthesis of oxazolidine-2,4-diones, Tetrahedron, 51, 5891, 10.1016/0040-4020(95)00257-9 Shine, 1996, The “thermal” rearrangement of hydrazo compounds. IV. The intramolecularity of the rearrangement1, J. Org. Chem., 61, 380 Yoshida, 1984, A direct synthesis of carbamate ester from carbon dioxide, amine and alkyl halide, Chem. Lett., 1571, 10.1246/cl.1984.1571 Yoshida, 1989, Novel synthesis of carbamate ester from carbon dioxide, amines, and alkyl halides, Bull. Chem. Soc. Jpn., 62, 1534, 10.1246/bcsj.62.1534 Salvatore, 2001, Efficient carbamate synthesis via a three-component coupling of an amine, CO2, and alkyl halides in the presence of Cs2CO3 and tetrabutylammonium iodide, J. Org. Chem., 66, 1035, 10.1021/jo001140u Salvatore, 2002, Efficient Cs2CO3-promoted solution and solid phase synthesis of carbonates and carbamates in the presence of TBAI, Tetrahedron, 58, 3329, 10.1016/S0040-4020(02)00286-7 Schilling, 2020, Transition metal-free synthesis of carbamates using CO2 as the carbon source, ChemSusChem, 13, 6246, 10.1002/cssc.202002073 Ghinet, 2010, Studies on pyrrolidinones. On the application of copper-catalyzed arylation of methyl pyroglutamate to obtain a new benzo[de]quinoline scaffold, Tetrahedron, 66, 215, 10.1016/j.tet.2009.10.103 Salvatore, 2002, Cesium effect: high chemoselectivity in direct N-alkylation of amines, J. Org. Chem., 67, 674, 10.1021/jo010643c Riemer, 2016, Chemoselective synthesis of carbamates using CO2 as carbon source, ChemSusChem, 9, 1916, 10.1002/cssc.201600521 https://www.co2.earth/, consulted on July 2020. pKa values were predicted using Chemicalize software (Chemaxon Ltd.). Kitulagoda, 2010, Synthesis of highly functionalized 2,5-disubstituted pyrrolidines via an aza-Morita–Baylis–Hillman-type reaction, Tetrahedron, 66, 6293, 10.1016/j.tet.2010.05.047 Hasbullah, 2010, Evaluating the use of chiral anthracene templates to access pyroglutamic acids, Tetrahedron Asymmetry, 21, 2719, 10.1016/j.tetasy.2010.10.021 Madar, 2006, J. Med. Chem., 49, 6416, 10.1021/jm060777o Prasad, 2012, A mechanism-based fluorescence transfer assay for examining ketosynthase selectivity, Org. Biomol. Chem., 10, 1992, 10.1039/c2ob06846j Huang, 2011, A facile approach to trans-4,5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine, Tetrahedron, 67, 7829, 10.1016/j.tet.2011.07.049 Peixoto, 2010, One-pot formation of Piperidine- and pyrrolidine-substituted pyridinium salts via addition of 5-Alkylaminopenta-2,4-dienals to N-Acyliminium ions: application to the synthesis of (±)-Nicotine and analogs, Org. Lett., 12, 4760, 10.1021/ol101783c Guo, 2008, Phosphinates as new electrophilic partners for cross-coupling reactions, Org. Biomol. Chem., 6, 4053, 10.1039/b809577a He, 2017, Diastereoselective synthesis and biological evaluation of enantiomerically pure tricyclic indolines, Org. Biomol. Chem., 15, 4241, 10.1039/C7OB00897J Schmidt, 1996, Enantioselective syntheses of (R)- and (S)-Hexahydropyridazine-3-carboxylic acid derivatives, Synthesis, 2, 223, 10.1055/s-1996-4192 Deguest, 2006, Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles, Tetrahedron Asymmetry, 17, 2120, 10.1016/j.tetasy.2006.07.039 Rigo, 1995, Studies on pyrrolidinones. Synthesis of some N‐fatty acylpyroglutamic acids, J. Heterocycl. Chem., 32, 1489, 10.1002/jhet.5570320513 Brown, 1991, Substitution reactions of 2-phenylsulphonyl-piperidines and -pyrrolidines with carbon nucleophiles: synthesis of the pyrrolidine alkaloids norruspoline and ruspolinone, Tetrahedron, 47, 1311, 10.1016/S0040-4020(01)86388-2 Poupaert, 2003, Unsymmetrical diarylketones from electron-rich heterocyclic arenes, Monatshefte fuer Chemie, 134, 823, 10.1007/s00706-002-0573-9 Sharifi, 2010, [Omim][BF4], a green and recyclable ionic liquid medium for the one-pot chemoselective synthesis of benzoxazinones, Tetrahedron Lett., 51, 1852, 10.1016/j.tetlet.2010.01.122