SELECTIVE PHOTOCYCLIZATION REACTIONS OF (Z)-N-ACETYL-alpha-DEHYDRO(9-PHENANTHRYL)ALANINE ALKYL ESTERS AND N ',N '-DIALKYLAMIDES TO DIBENZO[f,h]ISOQUINOLINE DERIVATIVES

(Z)-N-Acetyl-alpha-dehydro(9-phenanthryl)alanine alkyl esters and N',N'-dialkylamides [(Z)-1] were synthesized, and their photocyclization behavior in methanol was explored. The irradiation of (2)-1 in a protic polar solvent at wavelengths greater than 280 nm caused selective cyclization r...

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Bibliographic Details
Published inHeterocycles Vol. 89; no. 7; pp. 1678 - 1686
Main Authors Iijima, Yuto, Igarashi, Tetsutaro, Sakurai, Tadamitsu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2014
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ISOQUINOLINE
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Summary:(Z)-N-Acetyl-alpha-dehydro(9-phenanthryl)alanine alkyl esters and N',N'-dialkylamides [(Z)-1] were synthesized, and their photocyclization behavior in methanol was explored. The irradiation of (2)-1 in a protic polar solvent at wavelengths greater than 280 nm caused selective cyclization reactions, producing the corresponding dibenzo[f,h]isoquinoline derivatives. Moreover, the formation efficiency of these derivatives showed strong dependence on the steric bulk and electronic property of the alkoxycarbonyl and dialkylaminocarbonyl groups.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-14-13010