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Synthesis 2024; 56(14): 2263-2269
DOI: 10.1055/a-2270-0518
DOI: 10.1055/a-2270-0518
paper
Synthesis of Acyl Hydrazides and Hydrazones from Activated Amides
This study was financially supported by Chonnam National University (Grant number: 2023-0092-01).
Abstract
Acyl hydrazide and acyl hydrazone synthesis methods were developed. They involve the reaction of an activated amide with hydrazine under transition-metal-catalyst-free conditions. Additionally, acyl hydrazones were synthesized by extending the same reaction procedure in the presence of aldehydes (or ketones). These reactions were performed in an aqueous environment at 25 °C, demonstrating the successful attainment of the desired compounds with high yields.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2270-0518.
- Supporting Information
Publikationsverlauf
Eingereicht: 07. Januar 2024
Angenommen nach Revision: 15. Februar 2024
Accepted Manuscript online:
15. Februar 2024
Artikel online veröffentlicht:
06. März 2024
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References
- 1a Terzioglu N, Gursoy A. Eur. J. Med. Chem. 2003; 38: 781
- 1b Vicini P, Incerti M, Doytchinova IA, Colla PL, Bernadetta B, Loddo R. Eur. J. Med. Chem. 2006; 41: 624
- 1c Nasr T, Bondock S, Youns M. Eur. J. Med. Chem. 2014; 76: 539
- 1d Nasr T, Bondock S, Rashed HM, Fayad W, Youns M, Sakr TM. Eur. J. Med. Chem. 2018; 151: 723
- 1e Kalid W, Badshah A, Khan A.-U, Nadeem H, Ahmed S. Chem. Cent. J. 2018; 12: 11
- 1f Garkani-Nejad Z, Ahmadi-Roudi B. Eur. J. Med. Chem. 2010; 45: 719
- 1g Haiba NS, Khalil HH, Moniem MA, El-Wakil MH, Bekhit AA, Khattab SN. Bioorg. Chem. 2019; 89: 103013
- 1h Ajani OO, Iyaye KT, Aderohunmu DV, Olanrewaju IO, Germann MW, Olorunshola SJ, Bello BL. Arabian J. Chem. 2020; 13: 1809
- 1i Rohane SH, Chauhan AJ, Fuloria NK, Fuoria S. Arabian J. Chem. 2020; 13: 4495
- 1j Popiolek L. Med. Chem. Res. 2017; 26: 287
- 1k Moldovan CM, Oniga O, Parvu A, Tiperciuc B, Verite P, Pirnau A, Crisan O, Bojita M, Pop R. Eur. J. Med. Chem. 2011; 46: 526
- 1l Kadi AA, Al-Abdullah ES, Shehata IA, Habib EE, Ibrahim TM, El-Emam AA. Eur. J. Med. Chem. 2010; 45: 5006
- 1m Meira CS, dos Santos Filho JM, Sousa CC, Anjos PS, Cerqueira JV, Dias Neto HA, da Silveira RG, Russo HM, Wolfender J.-L, Queiroz EF, Moreira DR. M, Soares MB. P. Bioorg. Med. Chem. 2018; 26: 1971
- 1n Reddy AL. K, Kathale N. Orient. J. Chem. 2017; 33: 2930
- 1o Han S. Bull. Korean Chem. Soc. 2023; 44: 172
- 1p Vicini P, Zani F, Cozzini P, Doytchinova I. Eur. J. Med. Chem. 2002; 37: 553
- 1q Kucukguzel SG, Mazi A, Sahin F, Ozturk S, Stables J. Eur. J. Med. Chem. 2003; 38: 1005
- 1r Loncle C, Brunel JM, Vidal N, Dherbomez M, Letourneux Y. Eur. J. Med. Chem. 2004; 39: 1067
- 1s Masunari A, Tavares LC. Bioorg. Med. Chem. 2007; 15: 4229
- 2 Mali SN, Thorat BR, Gupta DR, Pangey A. Eng. Proc. 2021; 11: 21
- 3a Tynebor RM, Chen M.-H, Natarajan SR, O’Neill EA, Thompson JE, Fitzgerald CE, O’Keefe SJ, Doherty JB. Bioorg. Med. Chem. Lett. 2012; 22: 5979
- 3b Kim SB, Baek SE, Lim JH, Kim J. Bull. Korean Chem. Soc. 2022; 43: 1014
- 3c Aouad MR, Almehmadi MA, Albelwi FF, Teleb M, Tageldin GN, Abu-Serie MM, Hagar M, Rezki N. Bioorg. Chem. 2022; 124: 105816
- 4a Raparti V, Chitre T, Bothara K, Kumar V, Dangre S, Khachane C, Gore S, Deshmane B. Eur. J. Med. Chem. 2009; 44: 3954
- 4b Yan W, Ling L, Wu Y, Yang K, Liu R, Zhang J, Zhao S, Zhong G, Zhao S, Jiang H, Xie C, Cheng J. J. Med. Chem. 2021; 64: 16573
- 4c Brahmayya M, Dai SA, Suen S.-Y. RSC Adv. 2015; 5: 65351
- 4d Silalahi IH, Prokhorov AM, Tanner T, Cowling SJ, Whitwood AC, Bruce DW. J. Organomet. Chem. 2022; 977: 122455
- 4e Kahl DJ, Hutchings KM, Lisabeth EM, Haak AJ, Leipprandt JR, Dexheimer T, Khanna D, Tsou P.-S, Campbell PL, Fox DA, Wen B, Sun D, Bailie M, Neubig RR, Larsen SD. J. Med. Chem. 2019; 62: 4350
- 5a Wang Q, Liu L, Dong J, Tian Z, Chen T. New J. Chem. 2019; 43: 9384
- 5b Ye D, Liu Z, Chen H, Sessler JL, Lei C. Org. Lett. 2019; 21: 6888
- 5c Hie L, Fine Nathel NF, Shah TK, Baker EL, Hong X, Yang Y.-F, Liu P, Houk KN, Garg NK. Nature 2015; 524: 79
- 5d Liu Y, Meng G, Liu R, Szostak M. Chem. Commun. 2016; 52: 6841
- 5e Li X, Zou G. Chem. Commun. 2015; 51: 5089
- 6 Joseph D, Lee S. Org. Lett. 2022; 24: 6186
- 7 Singh S, Kandasamy J. Asian J. Org. Chem. 2023; 12: e202300115
- 8 Joseph D, Park MS, Lee S. Org. Biomol. Chem. 2021; 19: 6227
- 9 Ghodse SM, Takale BS, Hatvate NT, Telvekar VN. ChemistrySelect 2018; 3: 4168
- 10 Omodei-Salé A, Consonni P, Galliani G. J. Med. Chem. 1983; 26: 1187
- 11 Yavari I, Shaabanzadeh S. J. Org. Chem. 2022; 87: 15077
- 12 Herrera RP, Roca-López D, Navarro-Moros G. Eur. J. Org. Chem. 2010; 1450
- 13 dos Santos Filho JM. Eur. J. Org. Chem. 2014; 6411