The Synthesis of 7-Substituted-2,3-dihydropyrido [4,3-d] pyridazine-1,4-diones and 1,4-Dioxo-7-substituted1,2,3,4-tetrahydropyrido[4,3-d] pyridazine 6-Oxides from Methyl Ketones

被引：3

作者：

Prek, Benjamin ^{[1
]}

Stanovnik, Branko ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Vecna Pot 113,POB 537, Ljubljana 1000, Slovenia

来源：

ACTA CHIMICA SLOVENICA | 2017年 / 64卷 / 04期

关键词：

methyl ketones; 7-substituted-2,3-dihydropyrido[4,3-d] pyridazine-1,4-diones; 1,4-dioxo-7-substituted1,2,3,4-tetrahydropyrido[4,3-d] pyridazine 6-oxides; ELECTRON-POOR ACETYLENES; METAL-FREE SYNTHESIS; 2+2 CYCLOADDITION; APLYSINOPSIN ANALOGS; N-OXIDES; DERIVATIVES; PYRIDINE; ENAMINONES; 3-(DIMETHYLAMINO)PROPENOATES; HETEROCYCLES;

D O I：

10.17344/acsi.2017.3695

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general four-step transformation of alkyl, cycloalkyl, aryl, and heteroaryl methyl ketones via 3-(dimethylamino)-1-substituted- prop-2-en-1-ones, followed by microwave [2+ 2] cycloaddition of dimethyl acetylenedicarboxylate, cyclization of (2E, 3E)-2-[(dimethylamino) methylene]-3-(2-substituted) succinates with ammonia or hydroxylamine hydrochloride into 2-substituted-pyridine-4,5-dicarboxylates and their N-oxides and final cyclization with hydrazine hydrate into of 7-substituted-2,3-dihydropyrido[3,4-d] pyridazine-1,4-diones and 1,4-dioxo-7-substituted-1,2,3,4-tetrahydropyrido[4,3-d] pyridazine 6-oxides is shown.

引用

页码：798 / 803

页数：6

共 50 条

[31] A NEW SYNTHESIS OF 1-SUBSTITUTED 7-METHYL-2-OXO-4-THIOXO-1,2,3,4,5,6-HEXAHYDRO-7 H-PYRROLO[2,3-D]PYRIMIDINES AND 8-METHYL-2-OXO-4-THIOXO-1,2,3,4,5,6,7,8-OCTAHYDROPYRIDO[2,3-D]PYRIMIDINES
TAKAHATA, H
NAKAJIMA, T
YAMAZAKI, T
SYNTHESIS-STUTTGART, 1984, (08): : 703 - 704
[32] Investigations on the synthesis and pharmacological properties of amides of 7-methyl-3-phenyl-1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propyl]-2,4-dioxo-1,2,3,4-tetrahydropyrido[2,3-d]-pyrimidine-5-carboxylic acid
Sladowska, H
Sieklucka-Dziuba, M
Rajtar, G
Sadowski, M
Kleinrok, Z
FARMACO, 1999, 54 (11-12): : 773 - 779
[33] SYNTHESIS OF 3,4,5,6,7,8-HEXAHYDRO-2H-4A,8-ALKANOPYRIDO[4,3-D]PYRIMIDINES FROM N,N'-DIBENZYLIDENEPHENYLMETHANEDIAMINES AND SOME 2-SUBSTITUTED CYCLANONES
TAKAJO, T
KAMBE, S
SYNTHESIS-STUTTGART, 1982, (08): : 655 - 657
[34] Synthesis of 2-Aryl-7-Methyl-1-Phenyl-4-Selenoxo-1,4-Dihydro-Pyrano[4,3-d]Pyrimidin-5-One via a Three-Component Condensation
Talaei, Hamed
Mosslemin, Mohammad H.
Hassanabadi, Alireza
Mohebat, Razieh
POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (05) : 4299 - 4304
[35] Synthesis of 2-Aryl-7-Methyl-1-Phenyl-4-Thioxo-1,4-Dihydro-Pyrano[4,3-d]Pyrimidin-5-One via a Three-Component Condensation
Abreshteh, Mina
Ghazanfari, Dadkhoda
Hassanabadi, Alireza
Rastakhiz, Nahid
POLYCYCLIC AROMATIC COMPOUNDS, 2024, 44 (01) : 555 - 561
[36] SYNTHESIS OF 1-METHYL-3-BETA-D-RIBOFURANOSYLPYRAZOLO[4,3-D]-PYRIMIDIN-7(6H)-SELONE AND CERTAIN RELATED NUCLEOSIDES AND NUCLEOTIDES
UGARKAR, BG
ROBINS, RK
REVANKAR, GR
NUCLEOSIDES & NUCLEOTIDES, 1984, 3 (03): : 233 - 244
[37] Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one
Chem. Heterocycl. Compd., 10 (1238-1239):
[38] Synthesis of substituted imidazo[1,2-b]-1,2,4-triazolo[4,3-d]-1,2,4-triazepine and 4H-imidazo[1,2-b]-1,2,4-triazino[4,3-d]-1,2,4-triazepin-7-one
Kruglenko V.P.
Povstyanoi M.V.
Klyuev N.A.
Idzikovskii V.A.
Chemistry of Heterocyclic Compounds, 1997, 33 (10) : 1238 - 1239
[39] X-ray structure analysis of substituted 5-(2,3-dihydro-7-benzofuryl)-1-methylpyrazolo[4,3-d]pyrimidin-7-one (Biagra)
Voelter, W
Maichle-Mössmer, C
Khanfar, MA
El-Abadelah, MM
Sabri, SS
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1999, 54 (12): : 1602 - 1605
[40] ENVIRONMENTALLY BENIGN SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 6-(3-ARYL [1,8] NAPHTHYRIDIN-2-YL)-5,6,7,8-TETRAHYDROPYRIDO [2,3-d] PYRIDAZINE-5,8-DIONES
Mogilaiah, K.
Praveena, D.
Aara, Anjum
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 23 (03) : 261 - 266

← 1 2 3 4 5 →