This article is cited in 8 scientific papers (total in 8 papers)
Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline
Abstract:
The reaction of N-benzoyl-2-(cyclohex-2-en-1-yl)aniline 1 with molecular oxygen in the presence of NaHCO3 results in N-benzoyl-1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, which was isomerised to 1-phenyl-2a,3,4,5,5a,10a-hexahydro[1,3]oxazolo-[5,4,3-j,k]carbazol-10-ium iodide, whereas the reaction of amide 1 with molecular bromine results in dibromide, but the interaction with NBS leads to 4-bromo-6-phenyl-1,2,3,4,4a,11b-hexahydrodibenzo[d,f][1,3] oxazepine.
Document Type:
Article
Language: English
Citation:
R. R. Gataullin, R. R. Ishberdina, O. V. Shitikova, L. V. Spirikhin, T. V. Kazhanova, I. B. Abdrakhmanov, “Synthesis of 1-iodo-1,2,3,4,4a,9a-hexahydrocarbazole, 2a,3,4,5,5a,10a-hexahydrooxazolocarbazolium iodide and 4-bromo-1,2,3,4,4a,11b-hexahydrodibenzoxazepine from N-benzoyl-2-(cyclohex-2-en-1-yl)aniline”, Mendeleev Commun., 14:5 (2004), 219–221
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https://www.mathnet.ru/eng/mendc3885
https://www.mathnet.ru/eng/mendc/v14/i5/p219
This publication is cited in the following 8 articles:
Laura G. Rodríguez, Josep Bonjoch, Ben Bradshaw, “Synthesis of Alkaloids and Compounds Containing the 3,4‐Benzomorphan Scaffold”, Eur J Org Chem, 27:1 (2024)
R. R. Gataullin, “Formation of Benzo[e]cycloalk[g][1,4]oxazocinones by Reaction of N-Mesyl- or N-Tosyl-N-2-[(1-cycloalken-1-yl)phenyl]glycines with Molecular Bromine”, Russ J Gen Chem, 91:8 (2021), 1484
Rail R. Gataullin, “The first synthesis of benzo[e]cycloalk[g]oxazocinone atropisomers via lactonization of N-mesyl- or N-arylsulfonyl-N-[2-(1-cycloalken-1-yl)-6-methylphenyl]glycines”, Tetrahedron, 96 (2021), 132388
Adrian Schulte, Simon Janich, Ernst‐Ulrich Würthwein, Susumu Saito, Bernhard Wünsch, “Investigation of the Corey Bromolactamization with N‐Functionalized Allylamines”, Journal of Heterocyclic Chem, 53:6 (2016), 1827
N. A. Likhacheva, A. A. Korlyukov, R. R. Gataullin, “Synthesis of (3RS)- and (3SR)-acetoxy-(3aRS,8bSR)-N-acetyl-5-methoxy-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indoles”, Russ J Org Chem, 45:3 (2009), 394
R. R. Gataullin, “Synthesis of compounds containing a cycloalka[b]indole fragment”, Russ J Org Chem, 45:3 (2009), 321
R. R. Gataullin, N. A. Likhacheva, K. Yu. Suponitskii, I. B. Abdrakhmanov, “Reactions of N- and C-alkenylanilines: VIII. Synthesis of functionalized cycloalka[b]indoles from o-(cycloalk-2-en-1-yl)anilines”, Russ J Org Chem, 43:9 (2007), 1310
Rail R. Gataullin, Razida R. Ishberdina, Olga V. Shitikova, Leonid V. Spirikhin, Tat'jana V. Kazhanova, Ildus B. Abdrakhmanov, “Synthesis of 1‐Iodo‐1,2,3,4,4a,9a‐hexahydrocarbazole, 2a,3,4,5,5a,10a‐Hexahydrooxazolocarbazolium Iodide and 4‐Bromo‐1,2,3,4,4a,11b‐hexahydrodibenzoxazepine from N‐Benzoyl‐2‐(cyclohex‐2‐en‐1‐yl)aniline.”, ChemInform, 36:8 (2005)
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