An efficient synthesis of 6-benzyl-2-arylthieno[2,3-d]pyrimidin-4(3H)-ones catalyzed byHClinvolving aFriedel-Craftsalkylation reaction

被引：0

作者：

Pan, Wan-Chen ^{[1
]}

Wang, Yi-Chun ^{[1
]}

Li, Tuan-Jie ^{[1
]}

Liu, Jian-Quan ^{[1
]}

Wang, Xiang-Shan ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Jiangsu Key Lab Green Synth Funct Mat, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2020年 / 57卷 / 11期

关键词：

AQUEOUS-MEDIA; DERIVATIVES; ANTICANCER; APOPTOSIS; IODINE; HETEROCYCLES; ALKYLATION; COMPONENTS; INHIBITORS; DISCOVERY;

D O I：

10.1002/jhet.4107

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Aldehyde could undergo not only the subsequent condensation and cyclization with 2-aminothiophene-3-carboxamide to build a pyrimidine ring, but also a Friedel-Crafts alkylation reaction with thiophene moiety to give unexpected 6-benzyl-2-arylthieno[2,3-d]pyrimidin-4(3H)- ones in good yields catalyzed by concentrated HCl.

引用

页码：3970 / 3979

页数：10

共 50 条

[11] Efficient synthesis of thieno[2,3-d]pyrimidin-4(3H)-ones by a sequential aza-Wittig reaction/base catalyzed cyclization
Dai, Zhong-Xu
Chen, Hong
Liu, Ming-Guo
Ding, Ming-Wu
HETEROCYCLIC COMMUNICATIONS, 2011, 17 (5-6) : 197 - 201
[12] Efficient synthesis of 2-substituted thieno[2,3-d]pyrimidin-4(3H)-ones via an iminophosphorane
Fang, Zheng-Dong
Hu, Yang-Gen
Ding, Ming-Wu
HETEROATOM CHEMISTRY, 2008, 19 (03) : 266 - 270
[13] A selective synthesis of 2-alkylamino thieno[2,3-d]pyrimidin-4(3H)-ones
Sun, Shao-Fa
Yang, Xu-Hong
HETEROCYCLIC COMMUNICATIONS, 2007, 13 (06) : 367 - 370
[14] Copper-catalyzed consecutive reaction to construct quinazolin-4(3H)-ones and pyrido[2,3-d]pyrimidin-4(3H)-ones
Li, Ting
Chen, Minglu
Yang, Lei
Xiang, Zhengxin
Wang, Yongwei
Li, Fei
Chen, Dongyin
TETRAHEDRON, 2016, 72 (06) : 868 - 874
[15] PHOSPHORUS PENTOXIDE IN ORGANIC-SYNTHESIS .34. SYNTHESIS OF 3-ARYLTHIENO[2,3-D]PYRIMIDIN-4(3H)-IMINES AND THEIR REARRANGEMENT TO N-ARYLTHIENO[2,3-D]PYRIMIDIN-4-AMINES
MOGENSEN, J
JORGENSEN, A
PEDERSEN, EB
CHEMICA SCRIPTA, 1988, 28 (02): : 195 - 200
[16] A CONVENIENT PROCEDURE FOR THE PREPARATION OF 5,6-DIHYDRO-6-NITRO-5-PHENYLFURO[2,3-D]PYRIMIDIN-4(3H)-ONES AND 5-PHENYLFURO[2,3-D]PYRIMIDIN-4(3H)-ONES
DAUZONNE, D
ADAMLAUNAY, A
TETRAHEDRON, 1992, 48 (15) : 3069 - 3080
[17] Synthesis and evaluation of thieno[2,3-d]pyrimidin-4(3H)-ones as potential antitubercular agents
Borate, Hanumant B.
Annadate, Ritesh A.
Vagh, Sandip S.
Pisal, Mahesh M.
Deokate, Sagar B.
Arkile, Manisha A.
Jadhav, Nandadeep J.
Nawale, Laxman U.
Sarkar, Dhiman
MEDCHEMCOMM, 2015, 6 (12) : 2209 - 2215
[18] SYNTHESIS OF 2-AMINO AND 2-GUANIDINO-THIENO[2,3-D]PYRIMIDIN-4(3H)-ONES
RAJASEKHARAN, KN
THOMAS, L
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1983, 22 (01): : 76 - 77
[19] PYRIDOPYRIMIDINES .4. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF PYRIDO[2,3-D]PYRIMIDIN-4(3H)-ONES
DAVE, CG
SHAH, PR
SHAH, GK
JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1990, 67 (02) : 177 - 179
[20] Facile Synthesis of 2-Alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones
Zeng, Xiao-Hua
Liu, Min
Ding, Ming-Wu
He, Hong-Wu
SYNTHETIC COMMUNICATIONS, 2010, 40 (10) : 1453 - 1460

← 1 2 3 4 5 →