Ammonium Acetate-Promoted One-Pot Tandem Aldol Condensation/Aza-Addition Reactions: Synthesis of 2,3,6,7-Tetrahydro-1H-pyrrolo[3,2-c] pyridin-4(5H)-ones

被引:7
|
作者
Zhang, Zhiguo [1 ,3 ]
Gao, Xiaolong [1 ]
Wan, Yameng [1 ]
Huang, Yuanyuan [1 ]
Huang, Guoqing [2 ]
Zhang, Guisheng [1 ]
机构
[1] Henan Normal Univ, Henan Key Lab Organ Funct Mol & Drug Innovat, Collaborat Innovat Ctr Henan Prov Green Mfg Fine C, Key Lab Green Chem Media & React,Minist Educ,Sch C, Xinxiang 453007, Henan, Peoples R China
[2] Handan Purificat Equipment Res Inst, Handan 056027, Hebei, Peoples R China
[3] Northeast Normal Univ, Jilin Prov Key Lab Organ Funct Mol Design & Synth, Changchun 130024, Jilin, Peoples R China
来源
ACS OMEGA | 2017年 / 2卷 / 10期
关键词
INVESTIGATIONAL DRUG TAK-441; INTRAMOLECULAR CYCLIZATION; ACTIVATED CYCLOPROPANES; DOMINO REACTION; CATALYST-FREE; DERIVATIVES; INHIBITORS; OXIDATION; CASCADE; NH4OAC;
D O I
10.1021/acsomega.7b00626
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient tandem intermolecular one-pot aldol condensation/aza-addition reaction of 2-methyl-3-carbamoylpyrroles and aldehydes was developed for the synthesis of 2,3,6,7-tetrahydro-1H-pyrrolo[3,2-c] pyridin4(5H)-ones. The reaction proceeded using only 3.0 equiv of ammonium acetate promoter in green solvent poly(ethylene glycol)-400 at 100 degrees C to afford a series of pyrrolo[3,2-c] pyridinone derivatives in good to excellent yields.
引用
收藏
页码:6844 / 6851
页数:8
相关论文
共 50 条
  • [1] SYNTHESIS OF 3-CHLORO-1H-PYRROLO[3,2-C]PYRIDIN-4(5H)-ONE AND 4-CHLORO-1H-PYRROLO[3,2-C]PYRIDIN-4(5H)-ONE
    CRISTALLI, G
    FRANCHETTI, P
    GRIFANTINI, M
    NASINI, E
    VITTORI, S
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1988, 20 (03) : 285 - 289
  • [2] Catalyst-Free Domino Reaction of 1-Acryloyl-1-N-arylcarbamyl-cyclopropanes with Amines: One-Pot Approach to 2,3,6,7-Tetrahydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-ones
    Zhang, Zhiguo
    Zhang, Feisong
    Wang, Huanhuan
    Wu, Hao
    Duan, Xinyu
    Liu, Qingfeng
    Liu, Tongxin
    Zhang, Guisheng
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (12) : 2681 - 2686
  • [3] THE SYNTHESIS OF 1-SUBSTITUTED 6-AMINO-1H-PYRROLO-[3,2-C]PYRIDIN-4(5H)-ONES
    SCHNELLER, SW
    LUO, JK
    HOSMANE, RS
    DURRFELD, RH
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) : 1153 - 1155
  • [4] 6-AMINO-1H-PYRROLO[3,2-C]PYRIDIN-4(5H)-ONE (3,7-DIDEAZAGUANINE)
    SCHNELLER, SW
    LUO, JK
    HOSMANE, RS
    TETRAHEDRON LETTERS, 1980, 21 (33) : 3135 - 3138
  • [5] SYNTHESIS AND BIOLOGICAL EVALUATION OF 6-AMINO-1H-PYRROLO[3,2-C]PYRIDIN-4(5H)-ONE (3,7-DIDEAZAGUANINE)
    SCHNELLER, SW
    LUO, JK
    HOSMANE, RS
    DECLERCQ, E
    STOECKLER, JD
    AGARWAL, KC
    PARKS, RE
    SAUNDERS, PP
    JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (12) : 1737 - 1739
  • [6] Vilsmeier-Type Reaction of Dimethylaminoalkenoyl Cyclopropanes: One-Pot Access to 2,3-Dihydrofuro [3,2-c]pyridin-4(5H)-ones
    Huang, Peng
    Zhang, Ning
    Zhang, Rui
    Dong, Dewen
    ORGANIC LETTERS, 2012, 14 (01) : 370 - 373
  • [7] 1H-PYRROLO[3,2-C]PYRIDIN-4,6(5H,7H)DIONE (3,7-DIDEAZAXANTHINE)
    SCHNELLER, SW
    HOSMANE, RS
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (07) : 1291 - 1292
  • [8] CFL light promoted one-pot synthesis of pyrano[3,2-c]chromen-5(4H)-ones
    Nadaf, Ankusab Noorahmadsab
    Shivashankar, Kalegowda
    SYNTHETIC COMMUNICATIONS, 2018, 48 (07) : 809 - 815
  • [9] A one-pot synthesis of 2,3-dihydro-1H-pyrrolo[3,2-c]quinolines
    Tomaszewski, Miroslaw J.
    Whalley, Adam
    Hu, Yun-Jin
    TETRAHEDRON LETTERS, 2008, 49 (19) : 3172 - 3175
  • [10] Identification of 2-(4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridin-3-yl)-ethylamine derivatives as novel GnRH receptor antagonists
    Chen, Mi
    Guo, Zhiqiang
    Lanier, Marion C.
    Zhao, Liren
    Betz, Stephen F.
    Huang, Charles Q.
    Loweth, Colin J.
    Ashweek, Neil J.
    Liu, Xin-Jun
    Struthers, R. Scott
    Bradbury, Margaret J.
    Behan, James W.
    Wen, Jenny
    O'Brien, Zhihong
    Saunders, John
    Zhu, Yun-Fei
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (14) : 3845 - 3850