Convergent Domino Knoevenagel Hetero-Diels-Alder and Domino Oxidation Hetero-Diels-Alder Reactions Encountered in an Unexpected Formation of Novel 5-Aryl-1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-diones and 5-Aryl-2,3-dihydro-2-thioxo-1H-pyrano[2,3-d]pyrimidin-4(5H)-ones

被引：5

作者：

Zidar, Nace ^{[1
]}

Kikelj, Danijel ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Pharm, Ljubljana 1000, Slovenia

来源：

HELVETICA CHIMICA ACTA | 2011年 / 94卷 / 05期

关键词：

CASCADE REACTIONS; NATURAL-PRODUCTS; DERIVATIVES; ACID;

D O I：

10.1002/hlca.201000325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Convergent domino Knoevenagel hetero-Diels-Alder and domino oxidation hetero-Diels-Alder reactions, in which both diene and dienophile are formed under the same reaction conditions in situ, are described for the first time, and their application is demonstrated by a one-pot synthesis of novel 5-aryl-1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-diones and 5-aryl-2,3-dihydro-2-thioxo-1H-pyrano[2,3-d]pyrimidin-4(5H)-ones.

引用

页码：859 / 867

页数：9

共 50 条

[1] Effective synthesis of 7-amino-6-cyano-5-aryl-5H-pyrano[2,3-d]pyrimidine-2,4(1H,3H)-diones under microwave irradiation
Gao, Y
Tu, SJ
Li, TJ
Zhang, XJ
Zhu, SL
Fang, F
Shi, DQ
SYNTHETIC COMMUNICATIONS, 2004, 34 (07) : 1295 - 1299
[2] Application of the 2(5H)furanone motif in the synthesis of new thiopyrano[2,3-d]thiazoles via the hetero-Diels-Alder reaction and related tandem processes
Lozynskyi, Andrii
Zimenkovsky, Borys
Karkhut, Andriy
Polovkovych, Svyatoslav
Gzella, Andrzej K.
Lesyk, Roman
TETRAHEDRON LETTERS, 2016, 57 (30) : 3318 - 3321
[3] An efficient multicomponent synthesis of 1H-pyrano[2,3-d]pyrimidine-2,4(3H,5H)-dione derivatives and evaluation of their α-amylase and α-glucosidase inhibitory activity
Naik, Mamata Devendra
Bodke, Yadav D.
Prashantha, J.
Naik, Jayanth K.
JOURNAL OF CHEMICAL RESEARCH, 2021, 45 (3-4) : 228 - 236
[4] 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
[5] Derivatives of the condensed thieno[2,3-d]pyrimidines.: 20.: Synthesis of 2-substituted 5,6-dihydro-8H-pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-ones and 5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-ones
Mkrtchyan, AP
Noravyan, AS
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2006, (03): : 441 - 444
[6] Novel Route for the Synthesis of 5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-diones
Dige, Nilam C.
Mahajan, Prasad G.
Dhokale, Ramdas K.
Chinchkar, Sarika M.
Patil, Mayuri, V
Pore, Dattaprasad M.
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2019, 51 (06) : 553 - 565
[7] A SIMPLE APPROACH TO 7-AMINO-5H-PYRANO[2,3-D]-PYRIMIDINE-2,4-(1H,3H)DIONE DERIVATIVES
SHARANIN, YA
KLOKOL, GV
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1983, (02): : 277 - 277
[8] Pyranofuranones via Lewis acid mediated hetero-Diels-Alder reactions of 4-furan-2(5H)ones: A convergent route to the manoalide substructure
Lattmann, E
Coombs, J
Hoffmann, HMR
SYNTHESIS-STUTTGART, 1996, (01): : 171 - &
[9] 1,1′,3,3′,5,5′-Hexamethylspiro[furo[2,3-d]pyrimidine-6(5H),5′-pyrimidine]-2,2′,4,4′,6′(1H,3H,1′H,3′H,5′H)-pentaone
Pesyan, Nader Noroozi
Rastgar, Saeed
Hosseini, Yaser
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2009, 65 : O1444 - U3327
[10] Novel Method for the Synthesis of 1,5-Dihydro-2h-Chromeno[2,3-D]Pyrimidine-2,4(3h)-Diones
V. A. Osyanin
D. V. Osipov
S. A. Pavlov
Yu. N. Klimochkin
Chemistry of Heterocyclic Compounds, 2014, 50 : 1195 - 1198

← 1 2 3 4 5 →