Pd(II)-Catalyzed Three-Component Synthesis of Furo[2,3-d]pyrimidines from β-Ketodinitriles, Boronic Acids, and Aldehydes

被引：2

作者：

Dhara, Hirendra Nath ^{[1
]}

Das, Bubul ^{[1
]}

Barik, Dinabandhu ^{[1
]}

Manna, Supriya ^{[1
]}

Patel, Bhisma K. ^{[1
]}

机构：

[1] Indian Inst Technol Guwahati, Dept Chem, North Guwahati 781039, India

来源：

ORGANIC LETTERS | 2023年 / 25卷 / 50期

关键词：

CONSTRUCTION; DERIVATIVES; ALKYNES; FURAN; ADDITION/CYCLIZATION; INHIBITORS; DISCOVERY; ACCESS; KINASE;

D O I：

10.1021/acs.orglett.3c04017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-(II)-catalyzed three-component synthesis of 2,4,6-triarylfuro-[2,3-d]-pyrimidines from beta-ketodinitriles, boronic acids, and aldehydes has been developed. The participation of both nitrile (-CN) groups led to the concurrent construction of furo-pyrimidine via the formation of C-C, (CC)-C-, C-O, C-N, and (CN)-N- bonds. The compounds show excellent photoluminescence properties with absorption maxima ranging from 348 to 387 nm and emission from 468 to 533 nm. The synthetic utility of the protocol was further demonstrated through a few postsynthetic manipulations.

引用

页码：9070 / 9075

页数：6

共 50 条

[31] Ultrasound Assisted One-Pot Three-Component Reaction for Synthesis of Novel Functionalized 4-Thioxo-Pyrano[2,3-c]Pyrazoles, 5-Thioxo-Pyrano[2,3-d]Pyrimidines and 5-Thioxo-Pyrido[2,3-d]Pyrimidines Catalyzed by Triethylamine
Ali, Tarik E.
Assiri, Mohammed A.
POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (07) : 5860 - 5868
[32] An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium-catalyzed multi-component domino reaction
Prajapati, Dipak
Gohain, Mukut
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2
[33] Fused pyrimidines.: Part II:: Synthesis and antimicrobial activity of some furo[3,2-e]imidazo[1,2-c]pyrimidines and furo[2,3-d]pyrimidines
Bhuiyan, MMH
Rahman, KMM
Hossain, MK
Rahim, MA
Hossain, MI
CROATICA CHEMICA ACTA, 2005, 78 (04) : 633 - 636
[34] CLASSICAL AND NONCLASSICAL FURO[2,3-D]PYRIMIDINES AS NOVEL ANTIFOLATES - SYNTHESIS AND BIOLOGICAL-ACTIVITIES
GANGJEE, A
DEVRAJ, R
MCGUIRE, JJ
KISLIUK, RL
QUEENER, SF
BARROWS, LR
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (08) : 1169 - 1176
[35] Synthesis and biological evaluation of furo[2,3-d]pyrimidines as Akt1 kinase inhibitors
Kim, Se Young
Kim, Dong Jin
Yang, Beom Seok
Yoo, Kyung Ho
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2007, 28 (07) : 1114 - 1118
[36] Synthesis and biological evaluation of furo[2,3-d]pyrimidines as Akt1 kinase inhibitors
Life Sciences Research Division, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 130-650, Korea, Republic of
Bull. Korean Chem. Soc., 2007, 7 (1114-1118):
[37] Three-Component Pd/Cu-Catalyzed Cascade Reactions of Cyclic Iodoniums, Alkynes, and Boronic Acids: An Approach to Methylidenefluorenes
Zhu, Daqian
Wu, Yongcheng
Wu, Baojian
Luo, Bingling
Ganesan, A.
Wu, Fu-Hai
Pi, Rongbiao
Huang, Peng
Wen, Shijun
ORGANIC LETTERS, 2014, 16 (09) : 2350 - 2353
[38] A novel one-pot three-component reaction for the synthesis of 5-arylamino-pyrrolo[2,3-d]pyrimidines under microwave irradiation
Naidu, P. Seetham
Bhuyan, Pulak J.
RSC ADVANCES, 2014, 4 (20) : 9942 - 9945
[39] Enviro-economic, Ultrasound-assisted One-pot, Three-component Synthesis of Pyrido[2,3-d]pyrimidines in Aqueous Medium
Hussein, Essam M.
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2012, 67 (03): : 231 - 237
[40] One-pot three-component domino protocol for the synthesis of novel pyrano[2,3-d]pyrimidines as antimicrobial and anti-biofilm agents
Suresh, Lingala
Poornachandra, Y.
Kanakaraju, S.
Kumar, C. Ganesh
Chandramouli, G. V. P.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (26) : 7294 - 7306

← 1 2 3 4 5 →