The Preparation of Various New Heterocyclic Compounds via Cyclization of Substituted Derivatives of Phenacyl Esters of Hydrazonoacetic Acid

Radek Mělnický; Martin Grepl; Antonín Lyčka; Valerio Bertolasi; Lubomír Kvapil; Barbora Dvořáková; Pavel Hradil

doi:10.1055/s-0033-1339348

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(17): 2447-2457
DOI: 10.1055/s-0033-1339348

paper

The Preparation of Various New Heterocyclic Compounds via Cyclization of Substituted Derivatives of Phenacyl Esters of Hydrazonoacetic Acid

Radek Mělnický

^bFarmak a.s., Na Vlcinci 3, 77117 Olomouc, Czech Republic Fax: +4058231424 eMail: pavel.hradil@farmak.cz

,

Martin Grepl

^bFarmak a.s., Na Vlcinci 3, 77117 Olomouc, Czech Republic Fax: +4058231424 eMail: pavel.hradil@farmak.cz

,

Antonín Lyčka

^cResearch Institute for Organic Syntheses, Rybitvi 296, 533 54 Pardubice, Czech Republic

^dUniversity of Hradec Kralove, Faculty of Science, Rokitanského 62, 500 03 Hradec Králove 3, Czech Republic

,

Valerio Bertolasi

^eDipartimento di Chimica and Centro di Structturistica Diffrattometrica, University of Ferrara, Via L. Borsari 46, 441 00 Ferrara, Italy

,

Lubomír Kvapil

^bFarmak a.s., Na Vlcinci 3, 77117 Olomouc, Czech Republic Fax: +4058231424 eMail: pavel.hradil@farmak.cz

,

Barbora Dvořáková

^bFarmak a.s., Na Vlcinci 3, 77117 Olomouc, Czech Republic Fax: +4058231424 eMail: pavel.hradil@farmak.cz

,

Pavel Hradil*

^aDepartment of Organic Chemistry, Palacky University, Tr. 17. Listopadu 12, 771 46 Olomouc, Czech Republic

^bFarmak a.s., Na Vlcinci 3, 77117 Olomouc, Czech Republic Fax: +4058231424 eMail: pavel.hradil@farmak.cz

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A procedure for the preparation of derivatives of phenacyl hydrazonopropanoates and their application in the synthesis of various heterocycles has been developed. Not only is the preparation of indole derivatives described, but also a new method for the preparation of previously unknown pyridazine derivatives.

Key words

phenacyl esters - hydrazone - cyclization - indoles - pyridazine

Volltext

Referenzen

References
1 Hradil P, Vaněček J, Hlaváč J, Ševčík J. Collect. Czech. Chem. Commun. 1999; 64: 257
2 Hradil P, Krejčí P, Hlaváč J, Wiedermannová I, Lyčka A, Bertolasi V. J. Heterocycl. Chem. 2004; 41: 375
3 Hradil P, Jirman J. Collect. Czech. Chem. Commun. 1995; 60: 1375
4 Soural M, Hlaváč J, Hradil P, Fryšová I, Hajdúch M, Bertolasi V, Maloň M. Eur. J. Med. Chem. 2006; 41: 467
5 Hradil P, Hlaváč J, Lemr K. J. Heterocycl. Chem. 1999; 36: 141
6 Lopez SE, Rosales ME, Salazar J, Urdaneta N, Ferrer R, Angel JE. Heterocycl. Commun. 2003; 9: 345
7 Hradil P, Grepl M, Hlavac J, Soural M, Malon M, Bertolasi V. J. Org. Chem. 2006; 71: 819
8 Hradil P, Hlaváč J, Soural M, Hajdúch M, Kolář M, Večeřová R. Mini-Rev. Med. Chem. 2009; 9: 696
9 Mělnický R, Kvapil L, Šlézar P, Grepl M, Hlaváč J, Lyčka A, Hradil P. J. Heterocycl. Chem. 2008; 45: 1
10 Corson BB, Dodge A, Harris SA, Yeaw JS. Org. Synth. Coll. Vol. I . John Wiley & Sons; London: 1941: 336
11 Corson BB, Dodge A, Harris SA, Yeaw JS. Org. Synth. Coll. Vol. I . John Wiley & Sons; London: 1941: 241
12 Otwinowski Z, Minor Z In Methods in Enzymology . Vol. 276, Part A. Carter CW, Sweet RM. Academic Press; London: 1977: 307-326
13 Altomare A, Burla MC, Camalli M, Cascarano GL, Giacovazzo C, Guagliardi A, Moliterni AG, Polidori G, Spagna R. J. Appl. Crystallogr. 1999; 32: 115
14 Sheldrick GM. SHELXL97, Program for Crystal Structure Refinement . University of Göttingen; Göttingen: 1997
15 Nardelli M. J. Appl. Crystallogr. 1995; 28: 659
16 Farrugia LJ. J. Appl. Crystallogr. 1999; 32: 837
17 Burnett MN, Johnson CK. ORTEP-III: Oak Ridge Thermal Ellipsoids Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895. Oak Ridge National Laboratory; Oak Ridge (TN, USA): 1996
18 Hradil P, Mělnický R, Grepl M, Koristek K, Hlaváč J, Bertolasi V. Heterocycles 2006; 68: 9

Zusatzmaterial

Supporting Information