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

[21] Furo, Pyrano, and Pyrido[2,3-d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications
Rezaeifard, Amin
Bakherad, Mohammad
Navidpour, Latifeh
Bajestani, Mahsa Abedi
Onagh, Gohar
CHEMISTRYSELECT, 2024, 9 (10):
[22] Review on synthetic approaches towards barbituric acids-based furo[2,3-d]pyrimidines
Olyaei, Abolfazl
Sadeghpour, Mahdieh
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (11) : 1838 - 1863
[23] Rh(I)-catalyzed three-component reaction of 2,3-allenoates, organoboronic acids, and aldehydes.: An efficient synthesis of α,β-unsaturated δ-lactones
Bai, Tao
Ma, Shengming
Jia, Guochen
TETRAHEDRON, 2007, 63 (27) : 6210 - 6215
[24] One-pot, three-component Synthesis of pyrrolo[2,3-d]pyrimidine Derivatives
Javahershenas, Ramin
Khalafy, Jabbar
JOURNAL OF THE MEXICAN CHEMICAL SOCIETY, 2018, 62 (01)
[25] Chromeno[2,3-d]pyrimidine-triones Synthesis by a Three-Component Coupling Reaction
Ghahremanzadeh, Ramin
Fereshtehnejad, Fatemeh
Bazgir, Ayoob
CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (04) : 516 - 520
[26] Three-Component Regioselective Synthesis of Tetrahydrofuro[2,3-d] oxazoles and Their Efficient Conversion to Oxazoles
Ohura, Arisa
Itoh, Toshimasa
Ishida, Hiroaki
Saito, Akio
Yamamoto, Keiko
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (06) : 673 - 676
[27] Three-component, one-pot synthesis of pyrido[2,3-d]pyrimidine derivatives catalyzed by KF-alumina
Wang, XS
Zeng, ZS
Shi, DQ
Tu, SJ
Wei, XY
Zong, ZM
SYNTHETIC COMMUNICATIONS, 2005, 35 (14) : 1921 - 1927
[28] Using Kiwi Juice as a Green Biocatalyst for the Synthesis of Pyrano[2,3-d]pyrimidines in the Facile One-pot, Three-Component Reaction
Tata, Mohsen
Marandi, Ghasem
Marjani, Ahmad Poursattar
BIOINTERFACE RESEARCH IN APPLIED CHEMISTRY, 2023, 13 (01):
[29] Regioisomeric synthesis of dihydrofuro[2,3-d]pyrimidines in a diastereoselective manner involving nitrogen ylides in one-pot three-component reaction
Dutta, Leema
Sharma, Meenakshi
Bhuyan, Pulak J.
TETRAHEDRON, 2016, 72 (42) : 6654 - 6660
[30] Synthesis of pyrido[2,3-d]pyrimidines from aminopyrimidinecarbaldehydes
Perandones, F
Soto, JL
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (02) : 413 - 419

← 1 2 3 4 5 →