Homoallenyl azines in criss-cross cycloaddition reactions

J 2013

Homoallenyl azines in criss-cross cycloaddition reactions

GALETA, Juraj, Stanislav MAN, Aneta VALOUŠKOVÁ a Milan POTÁČEK

Základní údaje

Originální název

Homoallenyl azines in criss-cross cycloaddition reactions

Autoři

GALETA, Juraj (703 Slovensko, domácí), Stanislav MAN (203 Česká republika, domácí), Aneta VALOUŠKOVÁ (203 Česká republika, domácí) a Milan POTÁČEK (203 Česká republika, garant, domácí)

Vydání

Monatshefte fur Chemie, Austria, Springer-Verlag, 2013, 0026-9247

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Rakousko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 1.347

Kód RIV

RIV/00216224:14310/13:00065943

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1007/s00706-012-0865-7

UT WoS

000314333900014

Klíčová slova anglicky

1;3 Dipole; Dipolarophile ; Stereoselective synthesis; Heterocycles; Retro reactions

Štítky

AKR, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 4. 4. 2014 13:32, Ing. Andrea Mikešková

Anotace

V originále

Thermally initiated combined intra-intermolecular criss-cross cycloadditions of substituted nonsymmetrical allenyl azines with isocyanate or isothiocyanate dipolarophiles were investigated. Substituted 1,3,10-triazatricyclo[ 5.2.1.04,10]dec-6-en-2-ones or -dec-6-ene-2-thiones were obtained as the main products in moderate to very good yields. The thermal stabilities of the tricyclic adducts in reactions with the competing reactive dipolarophile dimethyl acetylenedicarboxylate were studied and are discussed. In some cases, substituted 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles were found as side products. This reaction showed high atomeconomy and in all caseswe observed the presence of one diastereoisomer and regioisomer only, which was clearly revealed by crystallographic analysis.

Návaznosti

GA203/09/1345, projekt VaV

Název: Allenový synthon v přípravě heterocyklických sloučenin

Investor: Grantová agentura ČR, Allenový synthon v přípravě heterocyklických sloučenin

Citovat

GALETA, Juraj, Stanislav MAN, Aneta VALOUŠKOVÁ a Milan POTÁČEK. Homoallenyl azines in criss-cross cycloaddition reactions. Monatshefte fur Chemie. Austria: Springer-Verlag, 2013, roč. 144, č. 2, s. 205-216. ISSN 0026-9247. Dostupné z: https://dx.doi.org/10.1007/s00706-012-0865-7.

@article{1072693,
   author = {Galeta, Juraj and Man, Stanislav and Valoušková, Aneta and Potáček, Milan},
   article_location = {Austria},
   article_number = {2},
   doi = {http://dx.doi.org/10.1007/s00706-012-0865-7},
   keywords = {1;3 Dipole; Dipolarophile ; Stereoselective synthesis; Heterocycles; Retro reactions},
   language = {eng},
   issn = {0026-9247},
   journal = {Monatshefte fur Chemie},
   title = {Homoallenyl azines in criss-cross cycloaddition reactions},
   url = {http://link.springer.com/article/10.1007/s00706-012-0865-7},
   volume = {144},
   year = {2013}
}

TY  - JOUR
ID  - 1072693
AU  - Galeta, Juraj - Man, Stanislav - Valoušková, Aneta - Potáček, Milan
PY  - 2013
TI  - Homoallenyl azines in criss-cross cycloaddition reactions
JF  - Monatshefte fur Chemie
VL  - 144
IS  - 2
SP  - 205-216
EP  - 205-216
PB  - Springer-Verlag
SN  - 00269247
KW  - 1;3 Dipole
KW  - Dipolarophile
KW  - Stereoselective synthesis
KW  - Heterocycles
KW  - Retro reactions
UR  - http://link.springer.com/article/10.1007/s00706-012-0865-7
N2  - Thermally initiated combined intra-intermolecular criss-cross cycloadditions of substituted nonsymmetrical allenyl azines with isocyanate or isothiocyanate dipolarophiles were investigated. Substituted 1,3,10-triazatricyclo[ 5.2.1.04,10]dec-6-en-2-ones or -dec-6-ene-2-thiones were obtained as the main products in moderate to very good yields. The thermal stabilities of the tricyclic adducts in reactions with the competing reactive dipolarophile dimethyl acetylenedicarboxylate were studied and are discussed. In some cases, substituted 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazoles were found as side products. This reaction showed high atomeconomy and in all caseswe observed the presence of one diastereoisomer and regioisomer only, which was clearly revealed by crystallographic analysis.
ER  -

GALETA, Juraj, Stanislav MAN, Aneta VALOUŠKOVÁ a Milan POTÁČEK. Homoallenyl azines in criss-cross cycloaddition reactions. \textit{Monatshefte fur Chemie}. Austria: Springer-Verlag, 2013, roč.~144, č.~2, s.~205-216. ISSN~0026-9247. Dostupné z: https://dx.doi.org/10.1007/s00706-012-0865-7.

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