Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism

被引：13

作者：

Ledenyova, I. V. ^{[1
]}

Falaleev, A. V. ^{[1
]}

Shikhaliev, Kh. S. ^{[1
]}

Ryzhkova, E. A. ^{[2
]}

Zubkov, F. I. ^{[2
]}

机构：

[1] Voronezh State Univ, Univ Skaya Pl 1, Voronezh 394006, Russia

[2] Peoples Friendship Univ Russia, Ul Miklukho Maklaya 6, Moscow 117198, Russia

来源：

RUSSIAN JOURNAL OF GENERAL CHEMISTRY | 2018年 / 88卷 / 01期

关键词：

ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylate; thiourea; ANRORC rearrangement; formylation; RING CONTRACTION REACTIONS; EXPANSION; DERIVATIVES; 4-CHLOROMETHYL-1,2,3,4-TETRAHYDRO-6-METHYL-2-OXOPYRIMIDINE-5-CARBOXYLATE;

D O I：

10.1134/S1070363218010115

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylates with thiourea in dimethylformamide involves ANRORC rearrangement (Addition of the Nucleophile, Ring Opening, and Ring Closure) followed by N-formylation to give N-{5-(4-oxo-8-phenyl-1,4-dihydropyrazolo[5,1-c][1,2,4]-triazin-3-yl)-1,3-triazol-2-yl}formamides whose structure was confirmed by X-ray analysis. The reaction mechanism has been studied by HPLC/MS.

引用

页码：73 / 79

页数：7

共 22 条

[1] TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].

ALLEN, FH ;

KENNARD, O ;

WATSON, DG ;

BRAMMER, L ;

ORPEN, AG ;

TAYLOR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19

[2] SOME RING EXPANSION-RING CONTRACTION REACTIONS OF ETHYL 4-CHLOROMETHYL-1,2,3,4-TETRAHYDRO-6-METHYL-2-OXOPYRIMIDINE-5-CARBOXYLATE [J].

ASHBY, J ;

GRIFFITHS, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (15) :607-608

[3] SOME BASE-CATALYZED RING EXPANSION AND RING EXPANSION-RING CONTRACTION REACTIONS OF ETHYL 4-CHLOROMETHYL-1,2,3,4-TETRAHYDRO-6-METHYL-2-OXOPYRIMIDINE-5-CARBOXYLATE [J].

ASHBY, J ;

GRIFFITHS, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (07) :657-662

[4] INTRAMOLECULAR MICHAEL-TYPE ADDITIONS .2. SYNTHESIS OF DERIVATIVES OF 7-THIA-2-AZABICYCLO[3.2.1]OCT-3-ENE, A NOVEL HETEROCYCLIC RING-SYSTEM [J].

BAGGS, MEM ;

GREGORY, B .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (08) :794-802

[5]

Barlett R. K., 1967, J CHEM SOC C, P1664, DOI 10.1039/J39670001664

[6] SYNTHESIS OF 1,3-DIAZEPINE DERIVATIVES BY RING EXPANSION OF ALKYL 4-CHLOROMETHYL-1,2,3,4-TETRAHYDRO-6-METHYL-2-OXOPYRIMIDINE-5-CARBOXYLATES [J].

BULLOCK, E ;

CARTER, RA ;

COCHRANE, RM ;

GREGORY, B ;

SHIELDS, DC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (05) :895-905

[7] REARRANGEMENT OF 4-CHLOROMETHYL-1,4-DIHYDROPYRIDINE DERIVATIVES TO PYRROLO[1,2-C]PYRIMIDINES [J].

BULLOCK, E ;

GREGORY, B ;

THOMAS, MT .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1977, 55 (04) :693-699

[8]

CLAREMON DA, 1986, SYNTHESIS-STUTTGART, P664

[9] FIRST EXAMPLE OF AN ANRORC REARRANGEMENT OF A PYRAZOLO[5,1-c][1,2,4]TRIAZINE INVOLVING A SIDE CHAIN [J].

Didenko, V. V. ;

Ledenyova, I. V. ;

Shestakov, A. S. ;

Shikhaliev, Kh. S. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2010, 46 (06) :770-772

[10] Condensed sulfur-containing pyridine systems 3.* Construction of penta- and hexacyclic heterocyclic systems by the cascade reaction of 3-cyanopyridine-2(1H)-thiones and 3-cyano-pyridine-2(1H)-thiolates with 8-chloromethyl-3-methyl-7-(2-oxo-2-phenylethyl)xanthene [J].

Dotsenko, V. V. ;

Sventukh, D. V. ;

Krivokolysko, S. G. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (09) :1397-1409

← 1 2 3 →