First Example of Copper(I) Catalyzed Decarboalkoxymethylation of Alkyl 2-[1-(Pyridin-2-yl)-1H-pyrrol-2-yl]acetates

被引:3
|
作者
Ali, Sk Asraf [1 ,2 ]
Bera, Anirban [1 ]
Manna, Susanta Kumar [1 ]
Santra, Subrata [2 ]
Molla, Mijanur Rahaman [2 ]
Samanta, Shubhankar [1 ]
机构
[1] Bidhannagar Coll, Dept Chem, Kolkata 700064, India
[2] Univ Calcutta, Dept Chem, Acharya Prafulla Chandra Rd, Kolkata 700009, India
关键词
Pyrrole; Decarboalkoxymethylation; Copper(I); Isolated intermediate; Open flask; CROSS-COUPLING REACTION; ARYL ESTERS; ACIDS; NICKEL; DECARBOXYLATION; PROTODECARBOXYLATION; TRANSFORMATIONS; CYCLIZATION; SILYLATION; CLEAVAGE;
D O I
10.1002/ejoc.202000331
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report an unprecedented functional group assisted decarboalkoxymethylation (-CH2CO2R) of N-pyridinyl pyrrolo esters by using air stable and cheap copper(I) catalyst. 2-formyl substituent of pyrrole unit is the key isolated intermediate for this novel transformation. This methodology is quick and tolerates a wide range of functional groups in open flask conditions. This protocol provides a large array of tricyclic N-pyridinyl 2, 5 unsubstituted fused pyrrole derivatives with high yield (up to 92 %).
引用
收藏
页码:2754 / 2760
页数:7
相关论文
共 50 条
  • [21] 1-(2,3,4,5,6-Pentamethylbenzyl)-2-(pyridin-2-yl)-1H-benzimidazole
    Angay, Firat
    Celik, Omer
    Barlik, Orhan
    Ulusoy, Mahmut
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O563 - +
  • [22] 1-[6-(6-Acetylpyridin-2-yl)pyridin-2-yl]ethanone
    Dogan, Huseyin Zekeriya
    Sengul, Abdurrahman
    Coles, Simon John
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1295 - U1773
  • [23] (4-Butoxyphenyl)(1H-pyrrol-2-yl)methanone
    Prakash, V.
    Kapoor, Kamini
    Prakash, M. Shet
    Gupta, Vivek K.
    Kant, Rajni
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1521 - +
  • [24] (4-Fluorophenyl)(1H-pyrrol-2-yl)methanone
    Prakash, V.
    Kapoor, Kamini
    Prakash, M. Shet
    Gupta, Vivek K.
    Kant, Rajni
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O2073 - +
  • [25] In Situ Synthesis of 4-[(2-Pyridin-2-yl)-1-(pyridin-2-yl) vinylthio] benzoic Acid and Its Copper Complex
    Liu Ming-Li
    Yin Yan-Yan
    Shi Wei
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2009, 30 (07): : 1290 - 1292
  • [26] 1,4-Bis{[2-(pyridin-2-yl)-1H-imidazol-1-yl]methyl}benzene dihydrate
    Cui, Rui-Hai
    Lan, Ya-Qian
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4515 - U3247
  • [27] Synthesis and Biological Activity of 1-(Substituted phenoxyacetoxy)1-(pyridin-2-yl or thien-2-yl) methylphosphonates
    Wang, Tao
    Wang, Wei
    Peng, Hao
    He, Hongwu
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (01) : 173 - 179
  • [28] 2-[({[Bis(pyridin-2-yl) methylidene]hydrazinecarbonyl}hydrazinylidene)(pyridin-2-yl)methyl]pyridinium tetrafluoroborate
    Zhang, Jie
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1874 - U1531
  • [29] 2-Cyano-N'-[1-(pyridin-2-yl)ethylidene]acetohydrazide
    Zhang, Xiao-Yi
    Han, Xiao-Lin
    Qian, Zhi-Bin
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O3203 - +
  • [30] 2-(1H-Pyrrolo[2,3-b]pyridin-2-yl)pyridine
    Huang, Ping-Hsin
    Wen, Yuh-Sheng
    Shen, Jiun-Yi
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2012, 68 : O1943 - +