(R/S)-Ethyl 2-Acetoxy-4-phenyl-4H-chromene-3-carboxylate

被引:0
|
作者
Petkova-Yankova, Nevena I. [1 ]
Koleva, Ana I. [1 ]
Nikolova, Rositca D. [1 ]
机构
[1] Sofia Univ St Kl Ohridski, Fac Chem & Pharm, Sofia 1164, Bulgaria
关键词
4H-chromens; coumarins; enol form; O-acylation;
D O I
10.3390/M1875
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple protocol for the preparation of O-acylated enol form (R/S)-ethyl-2-acetoxy-4-phenyl-4H-chromene-3-carboxylate 5 was presented. The compound was characterized by H-1-, C-13-and DEPT135 NMR spectra, including {H-1,H-1} COSY, {H-1,C-13} HSQC, {H-1,C-13} HMBC, and 2D-NOESY spectra. The preferred regioselectivity for O-acylation of 3,4-dihydrocoumarin 5 in the presence of substituent in the 4th position in the chroman ring and accounting for the steric hindrance of the ester group in the 3rd place was confirmed.
引用
收藏
页数:5
相关论文
共 50 条
  • [21] Synthesis of 2-amide-3-carboxylate-4-aryl-4H-chromene derivatives
    Zhi-gang Zeng
    Lan-ying Wang
    Yang Cao
    Yan-ping Luo
    Research on Chemical Intermediates, 2012, 38 : 1751 - 1760
  • [22] NOVEL PHOTOREACTIONS OF CHROMENE DERIVATIVES - THE PHOTOLYSIS OF 4-ACETOXY-H-2-CHROMENE
    CLIMENT, MJ
    GARCIA, H
    MIRANDA, MA
    PRIMO, J
    TETRAHEDRON, 1987, 43 (05) : 999 - 1002
  • [23] 4-Chlorophenyl 2-oxo-2H-chromene-3-carboxylate
    Guo, Xiao-Qiang
    Yan, Jun
    Gan, Ya
    Song, Qin
    Gou, Xiao-Jun
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O574 - U1208
  • [24] Ethyl 2-amino-3-ethoxycarbonyl-7,8-dimethyl-4-[4-(methylsulfanyl)phenyl]-5-oxo-4H-pyrano[3,2-c]chromene-3-carboxylate
    Lakshmi, S.
    Manvar, Dinesh
    Parecha, Alpesh
    Shah, Anamik
    Sridhar, M. A.
    Prasad, J. Shashidhara
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2006, 62 : O2163 - O2165
  • [25] Synthesis of ethyl 2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-4H/2H-chromene3-carboxylates by cycloaddition of ethyl 2-(azidomethyl)-4H-chromene-3-carboxylates with alkynes
    Mudulkar, Sairam
    Kolla, Sai Teja
    Bhimapaka, China Raju
    INDIAN JOURNAL OF CHEMISTRY, 2022, 61 (08): : 809 - 815
  • [26] Ethyl 4-(4-bromophenyl)-6-r-phenyl-2-oxocyclohex-3-ene-1-t-carboxylate
    Anuradha, N.
    Thiruvalluvar, A.
    Yuvaraj, C.
    Pandiarajan, K.
    Butcher, R. J.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1896 - U148
  • [27] Synthesis of pure methyl [(2S,3R,αR)-1-(3-bromo-4-methoxyphenyl)-3-(α-acetoxy)ethyl-4-oxoazetidin-2-carboxylate] and its enantiomer
    Sánta, Z
    Párkányi, L
    Németh, I
    Nagy, J
    Nyitrai, J
    TETRAHEDRON-ASYMMETRY, 2001, 12 (01) : 89 - 94
  • [28] Ethyl 2-amino-4-phenyl-4H-1-benzothieno[3,2-b]pyran-3-carboxylate
    Boughaleb, Adil
    Zouihri, Hafid
    Gmouh, Said
    Kerbal, Abdelali
    El Yazidi, Mohamed
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2106 - U1145
  • [29] Crystal structure of 4-bromophenyl-2-oxo-2H-chromene-3-carboxylate
    Devarajegowda, H. C.
    Suchetanp, P. A.
    Srinivasa, H. T.
    Sreenivasa, S.
    Palakshamurthy, B. S.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O326 - U481
  • [30] Ethyl 5-oxo-4-phenyl-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxylate
    Shubakara, K.
    Chandra
    Srikantamurthy, N.
    Mahendra, M.
    Umesha, K. B.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O661 - +