Peculiarities of the reactions of a,b-unsaturated g-bromoketones with hydrazine derivatives
DOI:
https://doi.org/10.17721/fujcV6I1P56-66Keywords:
1-aminopyrrole, a, b-unsaturated, g-bromoketones, cyclization, hydrazine, pyridazineAbstract
The reaction result of a,b-unsaturated g-bromoketones with hydrazines depends on the structure of the reagents. Reaction with hydrazine hydrate leads to the mixture of 3,5- di(R)pyridazine, 3,6-di(R)pyridazine and 2,4-di(R)-1H-pyrrol-1-amine derivatives. The formation of three types of products is due to the structure of the unsaturated aliphatic ketone. Two competing reaction schemes of ketones with hydrazines are considered, which include condensation or Michael-type addition in the first stage. The main products of the reactions of halogen-substituted derivatives of g-bromodipnone with arylhydrazines are 1,3,5-triaryl-1,6-dihydropyridazines, which easily form aromatic salts under reaction conditions (when heated in EtOH).References
Goller M, Barthet C, McCarthy G, Corradi R, Newby B, Wilson S, Armes S, Luk S. Synthesis and characterization of surface-aminated polypyrrole-silica nanocomposites. Colloid & Polymer Science 1998;276(11):1010-1018. https://doi.org/10.1007/s003960050340
Soganci T, Gumusay O, Soyleyici H, Ak M. Synthesis of highly branched conducting polymer architecture for electrochromic applications. Polymer 2018;134:187-195. https://doi.org/10.1016/j.polymer.2017.11.067
Suárez-Meneses J, Bonilla-Reyes E, Blé-González E, Ortega-Alfaro M, Toscano R, Cordero-Vargas A, López-Cortés J. Synthesis of [N,P] ligands based on pyrrole. Application to the total synthesis of arnottin I. Tetrahedron 2014;70(7):1422-1430. https://doi.org/10.1016/j.tet.2014.01.002
Son K, Park S. Synthesis of pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones: Rearrangement of pyrrolo[1,2-d][1,3,4]oxadiazines and regioselective intramolecular cyclization of 1,2-biscarbamoyl-substituted 1H-pyrroles. Beilstein Journal of Organic Chemistry 2016;12:1780-1787. https://doi.org/10.3762/bjoc.12.168
Jacobi P, Buddhu S, Fry D, Rajeswari S. Studies on the Synthesis of Phytochrome and Related Tetrapyrroles. Dihydropyrromethenones by Photochemical Rearrangement ofN-Pyrrolo Enamides. The Journal of Organic Chemistry 1997;62(9):2894-2906. https://doi.org/10.1021/jo970288j
Effland RC, Klein JT, inventors; Hoechst-Roussel Pharma. Inc., assignee. Pyrrolylaminopiperidines, compositions thereof and methods of use. United States patent 19854546105. 1985 Oct 8.
Attanasi O, Colombani S, De Crescentini L, Giorgi R, Monti S, Perrone A, Perrulli F, Renzetti A, Santeusanio S. Synthesis of biphenylyltetrazole derivatives of 1-aminopyrroles as angiotensin II antagonists. Il Farmaco 1999;54(1-2):64-76. https://doi.org/10.1016/s0014-827x(98)00100-1
Cirrincione G, Almerico AM, Aiello E. Pyrroles. In Jones RA, editor. The Chemistry of Heterocyclic Compounds. New York: Wiley; 1992 ,pp.315-323.
Poorand M, Anary-Abbasinejad M, Darehkordi A. A direct phosphine-mediated synthesis of polyfunctionalized 1-aminopyrroles from arylglyoxals, phenylhydrazine and acetylene diesters. Arkivoc 2017;2017(5):141-147. https://doi.org/10.24820/ark.5550190.p009.912
Du X, Xie X, Liu Y. Gold-Catalyzed Cyclization of Alkynylaziridines as an Efficient Approach toward FunctionalizedN-Phth Pyrroles. The Journal of Organic Chemistry 2010;75(2):510-513. https://doi.org/10.1021/jo902357x
Tang X, Shi M. An Efficient Route to 2-SubstitutedN-(1-Amino-3-methylpyrrol)amides by Ring-Opening Cyclization of Benzylidene- and Alkylidenecyclopropylcarbaldehydes with Hydrazides. The Journal of Organic Chemistry 2009;74(16):5983-5986. https://doi.org/10.1021/jo900730t
Kinjo R, Donnadieu B, Bertrand G. Gold-Catalyzed Hydroamination of Alkynes and Allenes with Parent Hydrazine. Angewandte Chemie International Edition 2011;50(24):5560-5563. https://doi.org/10.1002/anie.201100740
McLeod M, Boudreault N, Leblanc Y. Synthetic Application of Monoprotected Hydrazines toward the Synthesis of 1-Aminopyrroles. The Journal of Organic Chemistry 1996;61(3):1180-1183. https://doi.org/10.1021/jo9518260
Attanasi O, Filippone P. Working Twenty Years on Conjugated Azo-alkenes (and Environs) to Find New Entries in Organic Synthesis. Synlett 1997;1997(10):1128-1140. https://doi.org/10.1055/s-1997-973
Padwa A, Ku H. An unusual example of a 1,1-cycloaddition reaction of a diazoalkane. Tetrahedron Letters 1980;21(11):1009-1012. https://doi.org/10.1016/s0040-4039(00)78825-3
Goerlitzer K, Behrje H. 1,4-Dihydropyridazines, furanes and pyrroles with unlike ester groups related to Nifedipine. Pharmazie 1996;51(8):523-527.
Potikha L, Kovtunenko V, Turov A, Palamarchuk G, Zubatyuk R, Shishkin O, . Synthesis of 2,4-diphenyl-1H-pyrrol-1-amine derivatives. Chemistry of Heterocyclic Compounds 2009;45(3):327-335. https://doi.org/10.1007/s10593-009-0269-8
Gadzhily R, Fedoseev V, Netkacheva N, Akhmedov C, Sultanova M. Heterocyclization of 1-alkyl-4-chlorobut-2-en-1-ones with hydrazine hydrate. Chemistry of Heterocyclic Compounds 1989;25(7):837-837. https://doi.org/10.1007/bf00472762
Padwa A, Rodriguez A, Tohidi M, Fukunaga T. Intramolecular cycloaddition reactions of diazoalkenes. A theoretical prognosis of nitrene type behavior. Journal of the American Chemical Society 1983;105(4):933-943. https://doi.org/10.1021/ja00342a049
Ajello E. A new heterocycle: 2,7-dihydro-1,4,5-selenadiazepine. Journal of Heterocyclic Chemistry 1972;9(6):1427-1428. https://doi.org/10.1002/jhet.5570090645
Ito S, Kakehi A, Okada K. Degradational Cyclization of a-[2-Phenyl-2-(phenylsulfonylhydrazono)ethyl]phenacylidenetriphenylphosphoranes to 3,6-Diphenylpyridazines and 5-Benzoyl-3-phenylpyrazoles. HETEROCYCLES 1999;51(12):2949. https://doi.org/10.3987/com-99-8733
Singh R, Hay A. Synthesis and physical properties of poly(aryl ether phthalazine)s. Macromolecules 1992;25(3):1025-1032. https://doi.org/10.1021/ma00029a003
Sauer J, Heldmann D. Synthesis of 3,5-disubstituted pyridazines by regioselective [4+2] cycloadditions with ethynyltributyltin and subsequent replacement of the organotin substituent. Tetrahedron 1998;54(17):4297-4312. https://doi.org/10.1016/s0040-4020(98)00127-6
Auricchio S, Grassi S, Malpezzi L, Sarzi Sartori A, Truscello A. New Cleavage of the Azirine Ring by Single Electron Transfer: The Synthesis of 2H-Imidazoles, Pyridazines and Pyrrolines. European Journal of Organic Chemistry 2001;2001(6):1183-1187. https://doi.org/10.1002/1099-0690(200103)2001:6<1183::aid-ejoc1183>3.0.co;2-g
Potikha L, Kovtunenko V, Turov A, . Synthesis, structure, and properties of 1,3,5-triarylpyridazines. Chemistry of Heterocyclic Compounds 2009;45(7):815-822. https://doi.org/10.1007/s10593-009-0354-z
Oliver J, Waters R, Lusby W. Alkylation and rearrangement of lithiated 3-methyl-1,2-benzisoxazoles. The Journal of Organic Chemistry 1989;54(20):4970-4973. https://doi.org/10.1021/jo00281a050
Lemal D, Rave T. Pathways of n-aminopyrrole synthesis. Tetrahedron 1963;19(7):1119-1126. https://doi.org/10.1016/s0040-4020(01)98570-9
Attanasi O, Filippone P, Fiorucci C, Foresti E, Mantellini F. Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4H,5H)-Cyclopropylpyrazole Derivatives. The Journal of Organic Chemistry 1998;63(26):9880-9887. https://doi.org/10.1021/jo9816515
Uno H, Okada S, Suzuki H. Preparation of perfluoroalkyl azaarenes with a perfluoroalkyllithium-boron trifluoride system. Tetrahedron 1991;47(32):6231-6242. https://doi.org/10.1016/s0040-4020(01)86555-8
Lutz R, Slade L, Zoretic P. Base-induced Hydrolytic Rearrangement of trans-γ-Bromodypnone to 1,2-Dibenzoylethane1,2. The Journal of Organic Chemistry 1963;28(5):1358-1359. https://doi.org/10.1021/jo01040a050
Kulinkovich O, Tischenko I, Sorokin V. A New and Convenient Method of Synthesis of γ-Ketoaldehydes. Synthesis 1985;1985(11):1058-1059. https://doi.org/10.1055/s-1985-31427
Potikha L, Turelik A, Kovtunenko V. Synthesis and properties of z-1,3-bis-(aryl)-4-bromo-2-buten-1-ones. Chemistry of Heterocyclic Compounds 2009;45(10):1184-1189. https://doi.org/10.1007/s10593-010-0405-5
Potikha L, Turelyk A, Kovtunenko V, Turov A, Palamarchuk G, Zubatyuk R, Shishkin O. Interaction of (z)-4-bromo-1,3-di(2-thienyl)- 2-buten-1-one with amines, synthesis of di(2-thienyl)azolo[a]pyridines. Chemistry of Heterocyclic Compounds 2010;46(6):742-753. https://doi.org/10.1007/s10593-010-0578-y
Van Tamelen E, Whitesides T. Photolytic isomerization of aromatic species. Poly-tert-butylfurans. Journal of the American Chemical Society 1968;90(14):3894-3896. https://doi.org/10.1021/ja01016a071
Downloads
Published
Issue
Section
License
Copyright (c) 2018 French-Ukrainian Journal of Chemistry
This work is licensed under a Creative Commons Attribution 4.0 International License.
The French‑Ukrainian Journal of Chemistry holds copyright and publishes all articles under a Creative Commons Attribution 4.0 International licence (CC BY 4.0).
This license permits unrestricted use, sharing, adaptation, distribution, and reproduction in any medium or format, provided that the original author(s) and source are credited, a link to the license is included, and any changes made are indicated.
Authors grant the French‑Ukrainian Journal of Chemistry the exclusive right of first publication and may enter into separate, non‑exclusive distribution agreements for the published version (e.g., institutional repository, book chapter). Authors are also encouraged to post pre‑prints and post‑prints online to increase visibility and citation.
