Electron deficient heteroaromatic ammonioamidates-XVI1 1 For Part XV, see Ref. 1. The synthesis and photochemistry of ethyl N-(2-methyl-4-methylene-6,7-methylenedioxy- 3,4-dihydro-3-quinazolinyl)-N-phenylcarbamate

J. Fetter, Károly Lempert, Jørgen Møller

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3 Citations (Scopus)

Abstract

Irradiation through Pyrex of the N-(dihydroquinazolinyl)carbamate 3c in ethanol furnishes mixtures (Scheme 1) of two photoisomers (2c and 4a), two dimeric products: the 1,2-bis(4-quinazolinyl)ethane 5 and the (p-phenylene)dicarbamate 6, and of ethyl N-phenylcarbamate. The latter, as well as compounds 4a and 5 are formed also on irradiation of compound 2c. The radicals 9 and 10, formed by homolysis of the N-N bond of 3c as well as of the CH2-N bond of 2c are considered to be the primary photoproducts of both reactions, and to lead, by various recombination processes, to compounds 2c, 4a, 5 and 6, and to ethyl N-phenylcarbamate by hydrogen abstraction. It is not clear at present whether concerted photochemical [1,3] shifts contribute to the formation of 2c and 4a.

Original languageEnglish
Pages (from-to)2557-2563
Number of pages7
JournalTetrahedron
Volume34
Issue number16
DOIs
Publication statusPublished - 1978

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Phenylcarbamates
Photochemistry
Photochemical reactions
Irradiation
Electrons
Ethane
Carbamates
Genetic Recombination
Hydrogen
Ethanol
phenylurethane

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Electron deficient heteroaromatic ammonioamidates-XVI1 1 For Part XV, see Ref. 1. The synthesis and photochemistry of ethyl N-(2-methyl-4-methylene-6,7-methylenedioxy- 3,4-dihydro-3-quinazolinyl)-N-phenylcarbamate",
abstract = "Irradiation through Pyrex of the N-(dihydroquinazolinyl)carbamate 3c in ethanol furnishes mixtures (Scheme 1) of two photoisomers (2c and 4a), two dimeric products: the 1,2-bis(4-quinazolinyl)ethane 5 and the (p-phenylene)dicarbamate 6, and of ethyl N-phenylcarbamate. The latter, as well as compounds 4a and 5 are formed also on irradiation of compound 2c. The radicals 9 and 10, formed by homolysis of the N-N bond of 3c as well as of the CH2-N bond of 2c are considered to be the primary photoproducts of both reactions, and to lead, by various recombination processes, to compounds 2c, 4a, 5 and 6, and to ethyl N-phenylcarbamate by hydrogen abstraction. It is not clear at present whether concerted photochemical [1,3] shifts contribute to the formation of 2c and 4a.",
author = "J. Fetter and K{\'a}roly Lempert and J{\o}rgen M{\o}ller",
year = "1978",
doi = "10.1016/0040-4020(78)88386-0",
language = "English",
volume = "34",
pages = "2557--2563",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "16",

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TY - JOUR

T1 - Electron deficient heteroaromatic ammonioamidates-XVI1 1 For Part XV, see Ref. 1. The synthesis and photochemistry of ethyl N-(2-methyl-4-methylene-6,7-methylenedioxy- 3,4-dihydro-3-quinazolinyl)-N-phenylcarbamate

AU - Fetter, J.

AU - Lempert, Károly

AU - Møller, Jørgen

PY - 1978

Y1 - 1978

N2 - Irradiation through Pyrex of the N-(dihydroquinazolinyl)carbamate 3c in ethanol furnishes mixtures (Scheme 1) of two photoisomers (2c and 4a), two dimeric products: the 1,2-bis(4-quinazolinyl)ethane 5 and the (p-phenylene)dicarbamate 6, and of ethyl N-phenylcarbamate. The latter, as well as compounds 4a and 5 are formed also on irradiation of compound 2c. The radicals 9 and 10, formed by homolysis of the N-N bond of 3c as well as of the CH2-N bond of 2c are considered to be the primary photoproducts of both reactions, and to lead, by various recombination processes, to compounds 2c, 4a, 5 and 6, and to ethyl N-phenylcarbamate by hydrogen abstraction. It is not clear at present whether concerted photochemical [1,3] shifts contribute to the formation of 2c and 4a.

AB - Irradiation through Pyrex of the N-(dihydroquinazolinyl)carbamate 3c in ethanol furnishes mixtures (Scheme 1) of two photoisomers (2c and 4a), two dimeric products: the 1,2-bis(4-quinazolinyl)ethane 5 and the (p-phenylene)dicarbamate 6, and of ethyl N-phenylcarbamate. The latter, as well as compounds 4a and 5 are formed also on irradiation of compound 2c. The radicals 9 and 10, formed by homolysis of the N-N bond of 3c as well as of the CH2-N bond of 2c are considered to be the primary photoproducts of both reactions, and to lead, by various recombination processes, to compounds 2c, 4a, 5 and 6, and to ethyl N-phenylcarbamate by hydrogen abstraction. It is not clear at present whether concerted photochemical [1,3] shifts contribute to the formation of 2c and 4a.

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