Palladium catalysed coupling of iodoquinolines and acetylenes - A novel entry to the pyrrolo[3,2,1-ij]-quinoline nucleus

被引:0
|
作者
Blurton, P [1 ]
Brickwood, A [1 ]
Dhanak, D [1 ]
机构
[1] SmithKline Beecham Pharmaceut, Collegeville, PA 19426 USA
关键词
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 4-arylamino-8-iodoquinoline derivatives with propargyl alcohol and triethylamine in the presence of iodo(phenyl)bis(triphenylphosphine) palladium and copper(I)iodide gives 6-imino-substituted pyrrolo[3,2,-ij]quinolines under mild conditions and in moderate yields. Catalytic hydrogenation over Lindlar's catalyst affords functionalised 4H-pyrrolo[3,2,1-ij]quinolines in good yield.
引用
收藏
页码:2395 / 2403
页数:9
相关论文
共 50 条
  • [1] Pyrrolo[3,2,1-ij]quinolin-4-one and Pyrrolo[3,2,1-ij]quinolin-6-one
    McNab, Hamish
    Nelson, David J.
    Rozgowska, Emma J.
    SYNTHESIS-STUTTGART, 2009, (13): : 2171 - 2174
  • [2] Synthesis of a Variety of Activated Pyrrolo[3,2,1-ij ]quinolines
    Jumina
    Wenholz, Daniel S.
    Kumar, Naresh
    Black, David StC.
    SYNTHESIS-STUTTGART, 2019, 51 (09): : 1989 - 1994
  • [3] Spiro[pyrido[3,2,1-ij]pyrimido[4,5-b]quinoline-7,5-pyrrolo[2,3-d]pyrimidines] and Spiro[pyrimido[4,5-b]quinoline-5,1-pyrrolo[3,2,1-ij]quinolines] Derived from 5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione
    Baradarani, Mehdi M.
    Farshi, Hojat
    Khodaie, Maryam
    Fazlelahi, Hadi Zare
    Rashidi, Ahmad
    Joule, John A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (01) : 91 - 96
  • [4] NEW SYNTHESIS OF PYRROLO[3,2,1-IJ]QUINOLIN-4-ONE DERIVATIVES
    CHILIN, A
    RODIGHIERO, P
    PASTORINI, G
    GUIOTTO, A
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (03) : 980 - 983
  • [5] Hexahydrospiro-pyrazolo[3,4-b]pyridine-4,1-pyrrolo[3,2,1-ij]quinolines Derived from 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione
    Saatluo, Bahman Ebrahimi
    Baradarani, Mehdi M.
    Joule, John A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (05) : 1176 - 1182
  • [6] USE OF [2,3]-SIGMATROPIC REARRANGEMENTS IN A ONE-STEP CONVERSION OF TETRAHYDROQUINOLINE TO SUBSTITUTED 1,2,5,6-TETRAHYDRO-4H-PYRROLO[3,2,1-IJ]QUINOLIN-2-ONE AND 5,6-DIHYDRO-4H-PYRROLO[3,2,1-IJ]QUINOLINE
    GASSMAN, PG
    ROOS, JJ
    LEE, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (04) : 717 - 718
  • [7] Polymorphic modifications of a 1H-pyrrolo-[3,2,1-ij]quinoline-5-carboxamide possessing strong diuretic properties
    Shishkina, Svitlana V.
    Levandovskiy, Igor A.
    Ukrainets, Igor V.
    Sidorenko, Lyudmila V.
    Grinevich, Lina A.
    Yanchuk, Igor B.
    ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2018, 74 : 1759 - +
  • [8] A READY SYNTHESIS OF 4-OXO-4H-PYRROLO[3,2,1-IJ]QUINOLINES
    BLACK, DS
    IVORY, AJ
    KELLER, PA
    KUMAR, N
    SYNTHESIS-STUTTGART, 1989, (04): : 322 - 323
  • [9] An Efficient One-pot Synthesis of 4H-Pyrrolo[3,2,1-ij]quinolines
    Mehdi Adib
    Mohammad H. Sayahi
    Monatshefte für Chemie / Chemical Monthly, 2006, 137 : 207 - 211
  • [10] An Expedient Synthesis of Pyrrolo[3,2,1-ij]quinoline-1,2-diones via Intramolecular Friedel-Crafts Cyclization Protocol
    Moon, Hye Ran
    Kim, Su Yeon
    Lim, Jin Woo
    Kim, Jae Nyoung
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (11) : 2773 - 2776