Pyrrolidine and 1,3-oxazolidine formation from azomethine
ylides influenced by change from classical conditions to
microwave irradiation

J 2002

Pyrrolidine and 1,3-oxazolidine formation from azomethine ylides influenced by change from classical conditions to microwave irradiation

TRÁVNÍČEK, Martin a Milan POTÁČEK

Základní údaje

Originální název

Pyrrolidine and 1,3-oxazolidine formation from azomethine ylides influenced by change from classical conditions to microwave irradiation

Autoři

TRÁVNÍČEK, Martin (203 Česká republika) a Milan POTÁČEK (203 Česká republika, garant)

Vydání

ARKIVOC, Florida, ARKAT-USA, 2002, 1424-6376

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Kód RIV

RIV/00216224:14310/02:00005563

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

1;3-Dipolar cycloaddition; azomethine ylides; pyrrolidines; 1;3-oxazolidines; microwave initiation; mineral support; solvent free conditions

Štítky

1, 3-dipolar cycloaddition, 3-oxazolidines, Azomethine Ylides, microwave initiation, mineral support, pyrrolidines, solvent free conditions

Změněno: 18. 3. 2002 11:57, prof. RNDr. Milan Potáček, CSc.

Anotace

V originále

The reactions of ethyl N-alkylaminoacetates 1 in the presence of formaldehyde and dipolarophiles fumaronitrile and dimethylfumarate 3were investigated. They were followed and the results compared of reactions under classical heating and heating by MW either in solvent or without solvent or with solid supports. It has been found out that application of specific reaction conditions for the preparation of desired trisubstituted pyrrolidines 4a-4c and 5a-5c is dependent on the nature of the dipolarophile used. In the case of fumaronitrile the direct solventless reaction under microwave irradiation seems to be the most convenient method; in thecase of dimethyl fumarate mineral support (predominantly basic activated Al2O3) must be employed. In the absence of olefinic dipolarophile double bond C=O in a formaldehyde molecule serves as dipolarophile9 to form 1,3-oxazolidines 6a-6c. These are also by-products when toluene is used as a solvent.1 Yet in the case of addition of basic Al2O3 we do not observe oxazolidine formation and GC-MS analysis shows just a complex set of peaks.

Návaznosti

OC D10.20, projekt VaV

Název: Mikrovlnami aktivované chemické přeměny

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Mikrovlnami aktivované chemické přeměny

Citovat

TRÁVNÍČEK, Martin a Milan POTÁČEK. Pyrrolidine and 1,3-oxazolidine formation from azomethine ylides influenced by change from classical conditions to microwave irradiation. ARKIVOC. Florida: ARKAT-USA, 2002, roč. 2001, (V), s. 156-163. ISSN 1424-6376.

@article{399951,
   author = {Trávníček, Martin and Potáček, Milan},
   article_location = {Florida},
   article_number = {(V)},
   keywords = {1;3-Dipolar cycloaddition; azomethine ylides; pyrrolidines; 1;3-oxazolidines; microwave initiation; mineral support; solvent free conditions},
   language = {eng},
   issn = {1424-6376},
   journal = {ARKIVOC},
   title = {Pyrrolidine and 1,3-oxazolidine formation from azomethine ylides influenced by change from classical conditions to microwave irradiation},
   url = {http://www.arkat-usa.org/ark/journal/Volume2/Part3/Tisler/MT-316B/316B.htm},
   volume = {2001},
   year = {2002}
}

TY  - JOUR
ID  - 399951
AU  - Trávníček, Martin - Potáček, Milan
PY  - 2002
TI  - Pyrrolidine and 1,3-oxazolidine formation from azomethine ylides influenced by change from classical conditions to microwave irradiation
JF  - ARKIVOC
VL  - 2001
IS  - (V)
SP  - 156
EP  - 156
PB  - ARKAT-USA
SN  - 14246376
KW  - 1;3-Dipolar cycloaddition
KW  - azomethine ylides
KW  - pyrrolidines
KW  - 1;3-oxazolidines
KW  - microwave initiation
KW  - mineral support
KW  - solvent free conditions
UR  - http://www.arkat-usa.org/ark/journal/Volume2/Part3/Tisler/MT-316B/316B.htm
N2  - The reactions of ethyl N-alkylaminoacetates 1 in the presence of formaldehyde and dipolarophiles fumaronitrile and dimethylfumarate 3were investigated. They were followed and the results compared of reactions under classical heating and heating by MW either in solvent or without solvent or with solid supports. It has been found out that application of specific reaction conditions for the preparation of desired trisubstituted pyrrolidines 4a-4c and 5a-5c is dependent on the nature of the dipolarophile used. In the case of fumaronitrile the direct solventless reaction under microwave irradiation seems to be the most convenient method; in thecase of dimethyl fumarate mineral support (predominantly basic activated Al2O3) must be employed. In the absence of olefinic dipolarophile double bond C=O in a formaldehyde molecule serves as dipolarophile9 to form 1,3-oxazolidines 6a-6c. These are also by-products when toluene is used as a solvent.1 Yet in the case of addition of basic Al2O3 we do not observe oxazolidine formation and GC-MS analysis shows just a complex set of peaks.
ER  -

TRÁVNÍČEK, Martin a Milan POTÁČEK. Pyrrolidine and 1,3-oxazolidine formation from azomethine ylides influenced by change from classical conditions to microwave irradiation. \textit{ARKIVOC}. Florida: ARKAT-USA, 2002, roč.~2001, (V), s.~156-163. ISSN~1424-6376.

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