Photoenolization-Induced Oxirane Ring Opening in
2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising
Indanone Derivatives

J 2010

Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives

ŠOLOMEK, Tomáš, Peter ŠTACKO, Aneesh TAZHE VEETIL, Tomáš POSPÍŠIL, Petr KLÁN et. al.

Basic information

Original name

Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives

Name in Czech

Fotoenolizační otevření oxiranového kruhu u 2,5-dimethylbenzoyl oxiranů

Authors

ŠOLOMEK, Tomáš (703 Slovakia), Peter ŠTACKO (703 Slovakia, belonging to the institution), Aneesh TAZHE VEETIL (356 India, belonging to the institution), Tomáš POSPÍŠIL (203 Czech Republic) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)

Edition

Journal of Organic Chemistry, Columbus, OH, USA, the American Chemical Society, 2010, 0022-3263

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

United States of America

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 4.002

RIV identification code

RIV/00216224:14310/10:00044920

Organization unit

Faculty of Science

UT WoS

000283531100029

Keywords (in Czech)

Fotochemie; Fotoenolizace

Keywords in English

Photochemistry; Photoenolization

Abstract

ORIG CZ

V originále

Irradiation of 2,5-dimethylbenzoyl oxiranes results in a relatively efficient and high-yielding formation of beta-hydroxy functionalized indanones that structurally resemble biologically active pterosines. Nanosecond laser flash photolysis and quantum-chemical calculations based on density functional theory provided evidence that this photochemical transformation proceeds primarily via a photoenolization mechanism. Our study revealed considerable complexity of the mechanism and that structural modifications can significantly alter the reaction pathway and yield different products. The scope of this photochemical transformation for the synthesis of some pharmaceutically important compounds was investigated.

In Czech

Fotolýza 2,5-dimethylbenzoyl oxiranů vede k otevření oxiranového kruhu a následné tvorbě hydroxyindanonů.

Links

GA203/09/0748, research and development project

Name: Nové fotoaktivovatelné sloučeniny pro organickou chemii a biologii

Investor: Czech Science Foundation, New photoactivatable compounds for organic chemistry and biology

MSM0021622413, plan (intention)

Name: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment

Citovat

ŠOLOMEK, Tomáš, Peter ŠTACKO, Aneesh TAZHE VEETIL, Tomáš POSPÍŠIL and Petr KLÁN. Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives. Journal of Organic Chemistry. Columbus, OH, USA: the American Chemical Society, 2010, vol. 75, No 21, p. 7300-7309. ISSN 0022-3263.

@article{900530,
   author = {Šolomek, Tomáš and Štacko, Peter and Tazhe Veetil, Aneesh and Pospíšil, Tomáš and Klán, Petr},
   article_location = {Columbus, OH, USA},
   article_number = {21},
   keywords = {Photochemistry; Photoenolization},
   language = {eng},
   issn = {0022-3263},
   journal = {Journal of Organic Chemistry},
   title = {Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives},
   url = {http://pubs.acs.org/doi/abs/10.1021/jo101515a},
   volume = {75},
   year = {2010}
}

TY  - JOUR
ID  - 900530
AU  - Šolomek, Tomáš - Štacko, Peter - Tazhe Veetil, Aneesh - Pospíšil, Tomáš - Klán, Petr
PY  - 2010
TI  - Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives
JF  - Journal of Organic Chemistry
VL  - 75
IS  - 21
SP  - 7300-7309
EP  - 7300-7309
PB  - the American Chemical Society
SN  - 00223263
KW  - Photochemistry
KW  - Photoenolization
UR  - http://pubs.acs.org/doi/abs/10.1021/jo101515a
N2  - Irradiation of 2,5-dimethylbenzoyl oxiranes results in a relatively efficient and high-yielding formation of beta-hydroxy functionalized indanones that structurally resemble biologically active pterosines. Nanosecond laser flash photolysis and quantum-chemical calculations based on density functional theory provided evidence that this photochemical transformation proceeds primarily via a photoenolization mechanism. Our study revealed considerable complexity of the mechanism and that structural modifications can significantly alter the reaction pathway and yield different products. The scope of this photochemical transformation for the synthesis of some pharmaceutically important compounds was investigated.
ER  -

ŠOLOMEK, Tomáš, Peter ŠTACKO, Aneesh TAZHE VEETIL, Tomáš POSPÍŠIL and Petr KLÁN. Photoenolization-Induced Oxirane Ring Opening in 2,5-Dimethylbenzoyl Oxiranes To Form Pharmaceutically Promising Indanone Derivatives. \textit{Journal of Organic Chemistry}. Columbus, OH, USA: the American Chemical Society, 2010, vol.~75, No~21, p.~7300-7309. ISSN~0022-3263.

Detailed Information on Publication Record