One-pot synthesis of 3,4-dihydro-[1,3]oxazin-2-ones by BF3 Et2O-mediated approach of N-Boc phenylsulfonyl with ynamides

被引:0
|
作者
Wang, Rui-An [1 ]
Ren, Li-Zheng [1 ]
Han, Shi-Qing [1 ]
Wei, Bang-Guo [2 ]
机构
[1] Nanjing Tech Univ, Coll Biotechnol & Pharmaceut Engn, 30 Puzhu South Rd, Nanjing 211816, Peoples R China
[2] Fudan Univ, Sch Pharm, Dept Nat Med, 826 Zhangheng Rd, Shanghai 201203, Peoples R China
关键词
3,4-Dihydro-[1,3]oxazin-2-ones; BF3 & sdot; Et2O-mediated; N-Boc phenylsulfonyl; Ynamides; EFAVIRENZ;
D O I
10.1016/j.tetlet.2024.155222
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient one-pot approach to access functionalized 3,4-dihydro-[1,3]oxazin-2-one skeletons has been developed through BF3Et2O-mediated 3 Et 2 O-mediated addition-cyclization of ynamides and N- Boc phenylsulfones. The metal- free catalytic method exhibits good functional group compatibility. This study provides a practical new method for the synthesis of oxazinone skeletons.
引用
收藏
页数:5
相关论文
共 50 条
  • [1] One-pot synthesis of 4-methoxy(aralkoxy)imino-areno[1,3]oxazin-2-ones
    Kurz, T
    Widyan, K
    Wackendorff, C
    Schlüter, K
    SYNTHESIS-STUTTGART, 2004, (12): : 1987 - 1990
  • [2] One-pot synthesis of borolanes by reaction of aluminacyclopentanes with BF3·Et2O
    L. O. Khafizova
    L. I. Khusainova
    T. V. Tyumkina
    U. M. Dzhemilev
    Russian Journal of Organic Chemistry, 2012, 48 : 755 - 760
  • [3] One-pot synthesis of borolanes by reaction of aluminacyclopentanes with BF3•Et2O
    Khafizova, L. O.
    Khusainova, L. I.
    Tyumkina, T. V.
    Dzhemilev, U. M.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (06) : 755 - 760
  • [4] BF3•Et2O-mediated cascade cyclizations:: Synthesis of schweinfurthins F and G
    Mente, Nolan R.
    Neighbors, Jeffrey D.
    Wiemer, David F.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (20): : 7963 - 7970
  • [5] BF3•Et2O-mediated intramolecular cyclization of unsaturated amides: convenient synthesis of dihydroquinolin-2-one-BF2 complexes
    Liu, Xu
    Zhang, Qian
    Xin, Xiaoqing
    Zhang, Rui
    Zhang, Ning
    Liang, Yongjiu
    Dong, Dewen
    RSC ADVANCES, 2014, 4 (68) : 36234 - 36240
  • [6] Cu(OTf)2 catalyzed Biginelli type condensation of aldehydes, β-keto esters and carbamates:: Synthesis of 3,4-dihydro[1,3]oxazin-2-ones
    Jagdale, Arun R.
    Paraskar, Abhimanyu S.
    Sudalai, Arumugam
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (07): : 1091 - 1095
  • [7] One-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones using nano-cellulose/BF3/Fe3O4
    Maryam Alsadat Mazloum Tabaei
    Abdolhamid Bamoniri
    Bi Bi Fatemeh Mirjalili
    Journal of the Iranian Chemical Society, 2022, 19 : 2679 - 2691
  • [8] One-pot Biginelli synthesis of 3,4-dihydropyrimidin-2(1H)-ones using nano-cellulose/BF3/Fe3O4
    Tabaei, Maryam Alsadat Mazloum
    Bamoniri, Abdolhamid
    Mirjalili, Bi Bi Fatemeh
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2022, 19 (07) : 2679 - 2691
  • [9] Synthesis of 3-Sulfenylated Coumarins: BF3•Et2O-Mediated Electrophilic Cyclization of Aryl Alkynoates Using N-Sulfanylsuccinimides
    Gao, Wen-Chao
    Liu, Tao
    Zhang, Bing
    Li, Xing
    Wei, Wen-Long
    Liu, Qiang
    Tian, Jun
    Chang, Hong-Hong
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11297 - 11304
  • [10] Photochemical synthesis of 3,4-dihydro-2H-1,3-oxazin-4-ones
    Wessig, P
    Schwarz, J
    Lindemann, U
    Holthausen, MC
    SYNTHESIS-STUTTGART, 2001, (08): : 1258 - 1262