Photodecarboxylative cyclizations of ω-phthalimido-ortho-phenoxy carboxylates

Ae Rhan Kim; Kyoung Sub Lee; Cheon Woo Lee; Dong Jin Yoo; Fadi Hatoum; Michael Oelgemöller

doi:10.1016/j.tetlet.2005.03.090

Photodecarboxylative cyclizations of ω-phthalimido-ortho-phenoxy carboxylates

Ae Rhan Kim
, Kyoung Sub Lee
, Cheon Woo Lee
, Dong Jin Yoo^*
, Fadi Hatoum
, Michael Oelgemöller

^*Corresponding author for this work

Department of Biological Sciences

Jeonbuk National University
Seonam University
Dublin City University

Research output: Contribution to journal › Journal article › peer-review

18 Scopus citations

Abstract

ω-Phthalimido-ortho-phenoxy carboxylates efficiently undergo photodecarboxylative cyclizations in reasonable to good yields of 12-75%. Although the photocyclization efficiency decreases with increasing carbon chain lengths, target ring sizes up to 15 are successfully realized. Likewise, intermolecular photodecarboxylative additions of ω-phenoxy carboxylates to N-methyl phthalimide give hydroxyphthalimidines in yields of 45-73%.

Original language	English
Pages (from-to)	3395-3398
Number of pages	4
Journal	Tetrahedron Letters
Volume	46
Issue number	19
DOIs	https://doi.org/10.1016/j.tetlet.2005.03.090
State	Published - 2005.05.9

Keywords

Addition reactions
Cyclizations
Photodecarboxylation
Photoinduced electron transfer
Phthalimides

Quacquarelli Symonds(QS) Subject Topics

Engineering - Petroleum
Pharmacy & Pharmacology
Chemistry
Biological Sciences

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10.1016/j.tetlet.2005.03.090

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@article{bb2f5302e33045ef8db22cdf990fa9ca,

title = "Photodecarboxylative cyclizations of ω-phthalimido-ortho-phenoxy carboxylates",

abstract = "ω-Phthalimido-ortho-phenoxy carboxylates efficiently undergo photodecarboxylative cyclizations in reasonable to good yields of 12-75\%. Although the photocyclization efficiency decreases with increasing carbon chain lengths, target ring sizes up to 15 are successfully realized. Likewise, intermolecular photodecarboxylative additions of ω-phenoxy carboxylates to N-methyl phthalimide give hydroxyphthalimidines in yields of 45-73\%.",

keywords = "Addition reactions, Cyclizations, Photodecarboxylation, Photoinduced electron transfer, Phthalimides",

author = "Kim, \{Ae Rhan\} and Lee, \{Kyoung Sub\} and Lee, \{Cheon Woo\} and Yoo, \{Dong Jin\} and Fadi Hatoum and Michael Oelgem{\"o}ller",

year = "2005",

month = may,

day = "9",

doi = "10.1016/j.tetlet.2005.03.090",

language = "English",

volume = "46",

pages = "3395--3398",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "19",

}

TY - JOUR

T1 - Photodecarboxylative cyclizations of ω-phthalimido-ortho-phenoxy carboxylates

AU - Kim, Ae Rhan

AU - Lee, Kyoung Sub

AU - Lee, Cheon Woo

AU - Yoo, Dong Jin

AU - Hatoum, Fadi

AU - Oelgemöller, Michael

PY - 2005/5/9

Y1 - 2005/5/9

N2 - ω-Phthalimido-ortho-phenoxy carboxylates efficiently undergo photodecarboxylative cyclizations in reasonable to good yields of 12-75%. Although the photocyclization efficiency decreases with increasing carbon chain lengths, target ring sizes up to 15 are successfully realized. Likewise, intermolecular photodecarboxylative additions of ω-phenoxy carboxylates to N-methyl phthalimide give hydroxyphthalimidines in yields of 45-73%.

AB - ω-Phthalimido-ortho-phenoxy carboxylates efficiently undergo photodecarboxylative cyclizations in reasonable to good yields of 12-75%. Although the photocyclization efficiency decreases with increasing carbon chain lengths, target ring sizes up to 15 are successfully realized. Likewise, intermolecular photodecarboxylative additions of ω-phenoxy carboxylates to N-methyl phthalimide give hydroxyphthalimidines in yields of 45-73%.

KW - Addition reactions

KW - Cyclizations

KW - Photodecarboxylation

KW - Photoinduced electron transfer

KW - Phthalimides

UR - https://www.scopus.com/pages/publications/17144404149

U2 - 10.1016/j.tetlet.2005.03.090

DO - 10.1016/j.tetlet.2005.03.090

M3 - Journal article

AN - SCOPUS:17144404149

SN - 0040-4039

VL - 46

SP - 3395

EP - 3398

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Photodecarboxylative cyclizations of ω-phthalimido-ortho-phenoxy carboxylates

Abstract

Keywords

Quacquarelli Symonds(QS) Subject Topics

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