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The Darzens Condensation. II. Reaction of Chloroacetamides with Aromatic Aldehydes

Cite this: J. Org. Chem. 1963, 28, 6, 1514–1521
Publication Date (Print):June 1, 1963
https://doi.org/10.1021/jo01041a018
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    Cited By

    This article is cited by 24 publications.

    1. Susumu Oda and Hisashi Yamamoto . Synthesis of β-Hydroxy-α-haloesters through Super Silyl Ester Directed Syn-Selective Aldol Reaction. Organic Letters 2013, 15 (23) , 6030-6033. https://doi.org/10.1021/ol402928p
    2. Lilia Fuentes, Urbano Osorio, Leticia Quintero, Herbert Höpfl, Nixache Vázquez-Cabrera, and Fernando Sartillo-Piscil . Direct Chemical Method for Preparing 2,3-Epoxyamides Using Sodium Chlorite. The Journal of Organic Chemistry 2012, 77 (13) , 5515-5524. https://doi.org/10.1021/jo300542d
    3. Michael D. Delost, Jon T. Njardarson. Synthesis of Oxiranes and Aziridines from Aldehydes and Imines Using Anionic Homologation Approaches. 2023, 619-660. https://doi.org/10.1002/9783527830237.ch17
    4. V. K. Ahluwalia. Green Reactions. 2021, 35-277. https://doi.org/10.1007/978-3-030-58513-6_2
    5. V. A. Mamedov, V. L. Mamedova, G. Z. Khikmatova, D. E. Korshin, O. G. Sinyashin. 5-(α-Halobenzyl)- and 5-Benzylidene-2,2-dimethyl-1,3-oxazolidin-4-ones in Synthesis of α-Hydroxy Acids. Russian Journal of General Chemistry 2017, 87 (12) , 2801-2809. https://doi.org/10.1134/S1070363217120088
    6. Wei Huang, Hui Liu, Chong-Dao Lu, Yan-Jun Xu. Diastereoselective synthesis of 2-methoxyimidoyloxiranes via dimethyl phosphite-mediated coupling of α-keto N-sulfinyl imidates with aldehydes. Chemical Communications 2016, 52 (93) , 13592-13595. https://doi.org/10.1039/C6CC07723D
    7. Paola G. Gordillo, David M. Aparicio, Marcos Flores, Angel Mendoza, Laura Orea, Jorge R. Juárez, Gabriela Huelgas, Dino Gnecco, Joel L. Terán. Oxazolidine Sulfur Ylides Derived from Phenylglycinol for the Specific and Highly Diastereoselective Synthesis of Aryl and Alkyl trans ‐Epoxyamides. European Journal of Organic Chemistry 2013, 2013 (25) , 5561-5565. https://doi.org/10.1002/ejoc.201300732
    8. David M. Aparicio, Dino Gnecco, Jorge R. Juárez, María L. Orea, Angel Mendoza, Noemí Waksman, Ricardo Salazar, Marcos Fores-Alamo, Joel L. Terán. Diastereoselective synthesis of aryl and alkyl trans-glycidic amides from pseudoephedrine-derived sulfonium salt. Chemospecific exo-tet ring closure for morpholin-3-ones. Tetrahedron 2012, 68 (49) , 10252-10256. https://doi.org/10.1016/j.tet.2012.09.047
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    10. Nianchun Ma, Kemei Wu, Liang Huang. Study of the intramolecular cyclization of N-methyl-3-phenyl-N-(2-(E)-phenylethenyl)-trans(cis)-oxiranecarboxamide – Syntheses of Homoclausenamide and Dehydroclausenamide. European Journal of Medicinal Chemistry 2008, 43 (8) , 1781-1784. https://doi.org/10.1016/j.ejmech.2007.11.022
    11. Nianchun Ma, Kemei Wu, Liang Huang. An interesting cyclization of N ‐methyl‐3‐phenyl‐ N ‐(2‐( Z )‐phenylethenyl)‐ cis ‐oxiranecarboxamide. Journal of Heterocyclic Chemistry 2008, 45 (3) , 785-787. https://doi.org/10.1002/jhet.5570450324
    12. José M. Concellón, Juan A. Pérez-Andrés, Humberto Rodríguez-Solla. Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide. Chemistry - A European Journal 2001, 7 (14) , 3062-3068. https://doi.org/10.1002/1521-3765(20010716)7:14<3062::AID-CHEM3062>3.0.CO;2-F
    13. . G. 1997, 349-358. https://doi.org/10.1002/9783527625116.ch7
    14. Barbara Riemer, Otmar Hofer, Harald Greger. Tryptamine derived amides from Clausena indica. Phytochemistry 1997, 45 (2) , 337-341. https://doi.org/10.1016/S0031-9422(96)00848-5
    15. I. A. Nuretdinov, I. P. Karaseva, V. P. Gubskaya, K. M. Enikeev, A. V. Il'yasov. Reaction of myrtenal with dimethylamide of chloroacetic acid under the conditions of Darzens reaction. Russian Chemical Bulletin 1995, 44 (5) , 917-918. https://doi.org/10.1007/BF00696927
    16. Neal F. Osborne, Richard J. Atkins, Nigel J. P. Broom, Steven Coulton, John B. Harbridge, Michael A. Harris, Irene Stirling-François, Graham Walker. Synthesis of (5R)-(Z)-6-(1-methyl-1,2,3-triazol-4-ylmethylene)penem-3-carboxylic acid, a potent broad spectrum β-lactamase inhibitor, from 6-aminopenicillanic acid. J. Chem. Soc., Perkin Trans. 1 1994, 102 (2) , 179-188. https://doi.org/10.1039/P19940000179
    17. Richard P. Polniaszek, Stephen E. Belmont. Stereospecific Preparation of Transglycidic Esters. Synthetic Communications 1989, 19 (1-2) , 221-232. https://doi.org/10.1080/00397918908050973
    18. J. Ranfaing, B. Calas, J.M. Fabre, L. Giral. Stereochimie de la cyclisation du dibromo-1,3 butane et du dibromo-1,2 propane sur les sels metalliques du phenylacetonitrile. Tetrahedron Letters 1974, 15 (15) , 1439-1442. https://doi.org/10.1016/S0040-4039(01)82513-2
    19. Giancarlo Berti. Stereochemical Aspects of the Synthesis of 1,2‐Epoxides. 1973, 93-251. https://doi.org/10.1002/9780470147160.ch2
    20. B. Deschamps, J. Seyden-Penne. Effet de solvant sur la stereochimie de la reaction de darzens-III. Tetrahedron 1971, 27 (16) , 3959-3964. https://doi.org/10.1016/S0040-4020(01)98257-2
    21. H. Felkin, Y. Gault, G. Roussi. Stereochimie de quelques reactions entre aldehydes et reactifs de Grignard satures et allyliques. Tetrahedron 1970, 26 (15) , 3761-3778. https://doi.org/10.1016/S0040-4020(01)92953-9
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    23. . REFERENCES. 1969, 385-440. https://doi.org/10.1016/B978-0-08-022953-9.50033-8
    24. S. Bien, M. Ber, E. Flohr. The Reaction of N‐Bromoacetamide with α, β‐Unsaturated Carbonyl Compounds. I. Formation of Bromohydrins from 2‐Hydroxy‐ and 2′‐Hydroxychalcones. Israel Journal of Chemistry 1967, 5 (2) , 51-58. https://doi.org/10.1002/ijch.196700011

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