Photoinduced 1,2,3,4-tetrahydropyridine ring conversions

被引:2
|
作者
Turovska, Baiba [1 ]
Lund, Henning [2 ]
Lusis, Viesturs [1 ]
Lielpetere, Anna [1 ]
Liepins, Edvards [1 ]
Beljakovs, Sergejs [1 ]
Goba, Inguna [1 ]
Stradins, Janis [1 ]
机构
[1] Latvian Inst Organ Synth, Phys Organ Chem Lab, LV-1006 Riga, Latvia
[2] Aarhus Univ, Dept Organ Chem, DK-8000 Aarhus, Denmark
来源
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷
关键词
heterocyclic hydroperoxide; oxaziridine; photoinduced electron transfer; pyrrolidine; tetrahydropyridine; SUPEROXIDE ANION; HANTZSCH 1,4-DIHYDROPYRIDINES; OXIDATION; REDUCTION; OXYGEN; DIOXYGEN; KINETICS; ELECTRON; ANALOGS; COUPLE;
D O I
10.3762/bjoc.11.234
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stable heterocyclic hydroperoxide can be easily prepared as a product of fast oxidation of a 1,2,3,4-tetrahydropyridine by O-3(2) if the solution is exposed to sunlight. The driving force for the photoinduced electron transfer is calculated from electrochemical and spectroscopic data. The outcome of the reaction depends on the light intensity and the concentration of O-2. In the solid state the heterocyclic hydroperoxide is stable; in solution it is involved in further reactions.
引用
收藏
页码:2166 / 2170
页数:5
相关论文
共 50 条
  • [1] REACTION OF 1-NITROSO-1,2,3,4-TETRAHYDROPYRIDINE WITH MINERAL ACIDS
    LYLE, RE
    KRUEGER, WE
    GUNN, VE
    JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20): : 3574 - 3575
  • [2] STEREOCHEMISTRY OF THE 2-HYDROXY-1,2,3,4-TETRAHYDROPYRIDINE INTERMEDIATE OF HANTZSCH CYCLIZATION
    OGAWA, T
    MATSUMOTO, K
    YOSHIMURA, M
    HATAYAMA, K
    KITAMURA, K
    KITA, Y
    TETRAHEDRON LETTERS, 1993, 34 (12) : 1967 - 1970
  • [3] IMPROVED SYNTHESIS OF N-BENZYL-5-ETHYL-1,2,3,4-TETRAHYDROPYRIDINE
    NORMAN, MH
    HEATHCOCK, CH
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (14): : 3370 - 3371
  • [4] Synthesis and Antioxidative Properties of 1,2,3,4-Tetrahydropyridine Derivatives with Different Substituents in 4-Position
    Aiello, Daniele
    Jonas, Hendrik
    Carbone, Anna
    Carbone, Daniela
    Pecoraro, Camilla
    Tesoriere, Luisa
    Koehler, Jens
    Wuensch, Bernhard
    Diana, Patrizia
    MOLECULES, 2022, 27 (21):
  • [5] EPR spectra 3,3-disubstituted 1,2,3,4-tetrahydropyridine free radicals generated at electrochemical reduction
    Stradins, J
    Gavars, R
    Baumane, L
    Chekavichuius, B
    Duburs, G
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1998, (08): : 1103 - 1110
  • [6] SYNTHESIS OF NORMAL-BENZOYL-4-OXO-1,2,3,4-TETRAHYDROPYRIDINE AND ITS ETHYLENE KETAL
    SCHELL, FM
    WILLIAMS, PR
    SYNTHETIC COMMUNICATIONS, 1982, 12 (10) : 755 - 761
  • [7] Method of obtaining 6-ethoxycarbonylmethyl-sulfinyl-2,3-dihydroxy-1,2,3,4-tetrahydropyridine
    L. Krasnova
    A. Krauze
    S. Belyakov
    G. Duburs
    Chemistry of Heterocyclic Compounds, 2013, 48 : 1482 - 1486
  • [8] A CONVENIENT SYNTHESIS OF 6-ACETYL-1,2,3,4-TETRAHYDROPYRIDINE, THE PRINCIPLE BREAD FLAVOR COMPONENT
    DEKIMPE, N
    STEVENS, C
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10): : 2904 - 2906
  • [9] FORMATION OF A 3,3,5-TRICARBONYL-1,2,3,4-TETRAHYDROPYRIDINE DERIVATIVE UNDER THE HANTZSCH SYNTHESIS CONDITIONS
    CHEKAVICHUS, BS
    SAUSINSH, AE
    ZOLOTOYABKO, RM
    LIEPINSH, EE
    MAZHEIKA, IB
    DUBUR, GY
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (04): : 501 - 505
  • [10] Method of obtaining 6-ethoxycarbonylmethyl-sulfinyl-2,3-dihydroxy-1,2,3,4-tetrahydropyridine
    Krasnova, L.
    Krauze, A.
    Belyakov, S.
    Duburs, G.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 48 (10) : 1482 - 1486