Access to 2,3-Fused Pyrroles via Visible Light Driven Coupling of α-Azidochalcones with 1/2-Naphthols, or 2-Hydroxy-1,4-Naphthoquinone

被引：35
|
作者：
Borra, Satheesh [1 ,2 ]
Chandrasekhar, D. [1 ,2 ]
Newar, Uma Devi [1 ]
Maurya, Ram Awatar [1 ,2 ]
机构：
[1] NEIST, CSIR, Chem Sci & Technol Div, Appl Organ Chem Grp, Jorhat 785006, Assam, India
[2] NEIST, CSIR, Acad Sci & Innovat Res AcSIR, Jorhat 785006, Assam, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 02期
关键词：
ONE-POT SYNTHESIS; VINYL AZIDES; PHOTOREDOX CATALYSIS; CHEMICAL-SYNTHESIS; FUNCTIONALIZATION; DERIVATIVES; PRECURSORS;
D O I：
10.1021/acs.joc.8b02459
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
alpha-Azidochalcones were coupled with 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone using Ru(bpy)(3)(PF6)(2) as a photocatalyst under blue LED light irradiation to yield 2,3-fused pyrroles in high yields (68-84%). The overall transformation involves photosensitized decomposition of alpha-azidochalcones into highly reactive 2H-azirines which are trapped by 1/2-naphthols or 2-hydroxy-1,4-naphthoquinone, leading to the construction of two new C-N and one new C-C bonds.
引用
收藏
页码：1042 / 1052
页数：11
相关论文
共 50 条
  • [21] ON MODE OF INCORPORATION OF SHIKIMIC ACID INTO 2-HYDROXY-1,4-NAPHTHOQUINONE (LAWSONE)
    ZENK, MH
    LEISTNER, E
    ZEITSCHRIFT FUR NATURFORSCHUNG PART B-CHEMIE BIOCHEMIE BIOPHYSIK BIOLOGIE UND VERWANDTEN GEBIETE, 1967, B 22 (04): : 460 - &
  • [22] HEMOLYTIC-ACTIVITY AND NEPHROTOXICITY OF 2-HYDROXY-1,4-NAPHTHOQUINONE IN RATS
    MUNDAY, R
    SMITH, BL
    FOWKE, EA
    JOURNAL OF APPLIED TOXICOLOGY, 1991, 11 (02) : 85 - 90
  • [23] One-pot Synthesis of 2-Hydroxy-1,4-Naphthoquinone (Lawsone)
    Sivakumar, Dhanavel
    Thanusu, Jayaraman
    Kanagarajan, Vijayakumar
    Nagarajan, Samuthira
    Manikandan, Haridoss
    Gopalakrishnan, Mannathusamy
    CURRENT ORGANIC SYNTHESIS, 2019, 16 (03) : 431 - 434
  • [24] IMPROVED SYNTHESIS OF 2-HYDROXY-1,4-NAPHTHOQUINONE SULFONIC-ACIDS
    BAMFIELD, P
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1979, 11 (01) : 5 - 9
  • [25] Effect of butylated hydroxyanisole on the toxicity of 2-hydroxy-1,4-naphthoquinone to rats
    Munday, R
    Smith, BL
    Munday, CM
    CHEMICO-BIOLOGICAL INTERACTIONS, 1999, 117 (03) : 241 - 256
  • [26] On the oxidation of 2-hydroxy-1,4-naphthoquinone derivatives with alkaline potassium permanganate
    Hooker, SC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 : 1174 - 1179
  • [27] REACTION OF AMMONIA AND AMINES WITH A 2-HYDROXY-1,4-NAPHTHOQUINONE DERIVATIVE - 2-HYDROXY-N4-PHENYL-4-IMINO-1,4-NAPHTHOQUINONE (BETA-ANILINO-NAPHTHOQUINONE)
    LANTZ, R
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1972, (03): : 1052 - &
  • [28] Organocatalyzed Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-Ketophosphonatesθ
    Liu, Tao
    Wang, Youming
    Wu, Guiping
    Song, Haibin
    Zhou, Zhenghong
    Tang, Chuchi
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (10): : 4119 - 4124
  • [29] CORROSION INHIBITION AND ELECTRICAL-PROPERTIES OF 2-HYDROXY-1,4-NAPHTHOQUINONE (HNQ)
    MOHAMED, AK
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1991, (06): : 809 - 813
  • [30] Quantification of p-phenylenediamine and 2-hydroxy-1,4-naphthoquinone in henna tattoos
    Almeida, Pablo J.
    Borrego, Leopoldo
    Pulido-Melian, Elisenda
    Gonzalez-Diaz, Oscar
    CONTACT DERMATITIS, 2012, 66 (01) : 33 - 37
12345