Base-Mediated Regioselective Synthesis of Pyrrolo[3,4-b]quinolin-1-one and Benzo[b][1,6]Naphthyridin-1(2H)-One Derivatives from o-Alkynyl Quinoline-3-carbonitriles and Their Photophysical Properties

被引:2
作者
Kumar, Vipin [1 ,2 ]
Sharma, Shubham [3 ]
Pandey, Satyendra Kumar [4 ]
Singh, Virender [5 ]
机构
[1] Piramal Discovery Solut, Taluka Sanand 382213, Gujarat, India
[2] Dr BR Ambedkar NIT Jalandhar, Dept Chem, Jalandhar 144008, Punjab, India
[3] GLA Univ, Dept Chem, Mathura 281406, UP, India
[4] Banaras Hindu Univ, Dept Chem, Varanasi 221005, Uttar Pradesh, India
[5] Cent Univ Bathinda, Dept Chem, Ghudda 151401, Punjab, India
关键词
Cyclization; Fluorescence; Nitrogen heterocycles; Pyrrolo[3,4-b]quinolin-1-ones; Quinolines; FACILE SYNTHESIS; QUINOLINE; CYCLIZATION; ACCESS; PYRROLOQUINOLINES; ALKYNYLALDEHYDES; OXIDATION; ALDEHYDES; HYDRATION; IODINE;
D O I
10.1002/ejoc.202400582
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A (KOBu)-Bu-t-promoted robust strategy has been described for the regioselective synthesis of pyrrolo[3,4-b]quinolin-1-one and naphthyridin-1(2H)-one derivatives from o-alkynylquinolinecarbonitriles in good to excellent yields. The reaction proceeds through in situ transformation of the nitrile moiety into an amide group followed by the selective C-N bond formation through a 5-exo-dig or 6-endo-dig annulation reaction. Among the synthesized derivatives, 6-endo-dig naphthyridin-1(2H)-ones displayed good photophysical properties. The present approach is superior to other established methodologies as it avoids use of transition metals and column chromatographic purification and affords the products in high yields. Additionally, the current methodology provides several additional advantages, such as one-pot operation, high atom economy, broad substrate scope and a step-economical process.
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页数:9
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