Photochemical synthesis of 3,4-dihydro-2H-1,3-oxazin-4-ones

被引：0
|
作者：
Wessig, P. [1 ]
Schwarz, J. [1 ]
Lindemann, U. [1 ]
Holthausen, M.C. [1 ]
机构：
[1] Institut für Organische und Bioorganische Chemie, Humboldt-Universität zu Berlin, Hessische Straße 1-2, 10115 Berlin, Germany
来源：
Synthesis | 2001年 / 08期
关键词：
Carbon - Carbonylation - Chemical bonds - Oxygen;
D O I：
10.1055/s-2001-15061
中图分类号：
学科分类号：
摘要：
The first example of a C - O bond formation in the course of the Norrish - Yang reaction is described. Starting with readily accessible α-mesyloxy-β-keto amides 4, a δ-hydrogen transfer to the excited carbonyl group occurs and the diradicals thus formed undergo a very rapid elimination of methane sulfonic acid providing enolate diradicals. These ambidental enolate diradicals undergo a regioselective cyclization to 3,4-dihydro-2H-1,3-oxazin-4-ones 5. In two cases a cleavage reaction is observed, giving cyclic imines. The mechanism is investigated by means of DFT- and ab initio methods.
引用
收藏
页码：1258 / 1262
相关论文
共 50 条
  • [21] FACILE SYNTHESIS OF SUBSTITUTED PYRIMIDINES BY RING TRANSFORMATION OF 1,3-OXAZIN-4-ONES
    YAMAMOTO, Y
    AZUMA, Y
    HETEROCYCLES, 1977, 6 (11) : 1817 - 1820
  • [22] A Quick Route for the Synthesis of 3-Aryl-3,4-dihydro-2H-benz[e]-1,3-oxazin-2-ones
    Shukla, Davender Kumar
    Rani, Manju
    Khan, Arif Ali
    ASIAN JOURNAL OF CHEMISTRY, 2013, 25 (08) : 4537 - 4540
  • [23] First synthetic method for the preparation of 6-unsubstituted-2,3-dihydro-1,3-oxazin-4-ones
    Bertolini, G
    Aquino, M
    Ferrario, F
    Pavich, G
    Zaliani, A
    Sala, A
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10): : 3358 - 3361
  • [24] UNEXPECTED FORMATION OF 6-ARYL-2-TRIPHENYLPHOSPHINIMINO-1,3-OXAZIN-4-ONES
    NEKRASOV, DD
    ANDREICHIKOV, YS
    RAKITIN, OA
    ZHURNAL ORGANICHESKOI KHIMII, 1992, 28 (06): : 1319 - 1320
  • [25] Synthesis of 3,4-Dihydro-2H-1,3,5-thiadiazines
    Katritzky, AR
    Vakulenko, AV
    Xu, YJ
    Steel, PJ
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (14): : 4960 - 4962
  • [26] The Synthesis of Multifunctionalized 1,3-Oxazin-4-ones from Donor-Acceptor Cyclopropanes
    Smith, Robert J.
    Mills, Daniel A.
    Nhu, Duong
    Tan, Eng Wui
    Lucas, Nigel T.
    Hawkins, Bill C.
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (05): : 2099 - 2105
  • [27] Synthesis of heterocyclic substituted amidines starting from heterocyclo-1,3-oxazin-4-ones
    Briel, D
    PHARMAZIE, 1998, 53 (10): : 722 - 723
  • [28] TRIMETHYLCHLOROSILANE-CARBOXYLIC COMPOUND SYSTEMS IN THE SYNTHESIS OF OXAZOLIDINONES AND BENZO-[2H]-1,3-OXAZIN-4-ONES
    SHIPOV, AG
    ORLOVA, NA
    NOVIKOVA, OP
    BAUKOV, YI
    ZHURNAL OBSHCHEI KHIMII, 1985, 55 (04): : 943 - 944
  • [29] CATALYTIC-HYDROGENATION OF TETRAHYDRO-4H-1,3-OXAZIN-4-ONES AND 4-OXAZOLIDINONES
    ITO, K
    SEKIYA, M
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1972, 20 (08) : 1762 - +
  • [30] SYNTHESIS OF 2,3,6-TRISUBSTITUTED 3,4-DIHYDRO-4H-1,3-OXAZINE-4-ONES
    ANDREICHIKOV, YS
    KOZMINYKH, VO
    IONOV, YV
    SARAEVA, RF
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1978, (02): : 271 - 272
12345