The intramolecular photocyclization and photoreduction of 2-halo-N-pyridinylbenzamide

Nam Woong Song, Dongho Kim, Yong Tae Park, Chang Hee Jung, Kwang Wook Kim

Research output: Chapter in Book/Report/Conference proceedingConference contribution

Abstract

The intramolecular photocyclization of aryl halide has been investigated in relation to the synthetic method and the reaction mechanism. It is reported that heterocyclic molecular systems are formed from the photocyclization of haloarene tethered to arene by several linkages and a photohomolytic radical mechanism is involved in the photocyclization of N-phenylalkyl-2-halopyridinium and N-(2-halophenyl)alkyl pyridinium salts. In conjunction with the study of the heterocyclic ring formation, we observed that photoreaction of N-(2-halophenyl)pyridinecarboxamide in a basic medium produced an intramolecular photosubstitution product, 2-pyridinylbenzoxazole, instead of a photocyclization product, whereas photoreaction of 2-chloro-N-pyridinylbenzamide in a weak basic or neutral medium afforded an intramolecular photocyclization product, benzo[c]naphthyridinones. These reactions are straightforward and valuable for the syntheses of heterocyclic compounds such as benzoxazole and benzonaphthyridinone derivatives. Thus, it is desirable to develop the synthetic methods of the heterocyclic compounds and to clarify their reaction mechanisms. In this work, we have studied the photochemical reaction mechanism of 2-halo-N-pyridinylbenzamide by using a nanosecond laser flash photolysis technique.

Original languageEnglish
Title of host publicationCLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics
PublisherInstitute of Electrical and Electronics Engineers Inc.
Pages346-347
Number of pages2
Volume2
ISBN (Electronic)0780356616, 9780780356610
DOIs
Publication statusPublished - 1999 Jan 1
Event1999 Pacific Rim Conference on Lasers and Electro-Optics, CLEO/Pacific Rim 1999 - Seoul, Korea, Republic of
Duration: 1999 Aug 301999 Sep 3

Other

Other1999 Pacific Rim Conference on Lasers and Electro-Optics, CLEO/Pacific Rim 1999
CountryKorea, Republic of
CitySeoul
Period99/8/3099/9/3

Fingerprint

Heterocyclic Compounds
Photochemical reactions
Photolysis
photochemical reactions
halos
Benzoxazoles
Salts
Derivatives
heterocyclic compounds
Lasers
products
linkages
halides
flash
photolysis
salts
rings
synthesis
lasers

All Science Journal Classification (ASJC) codes

  • Electronic, Optical and Magnetic Materials
  • Atomic and Molecular Physics, and Optics
  • Computer Networks and Communications
  • Physics and Astronomy(all)

Cite this

Song, N. W., Kim, D., Park, Y. T., Jung, C. H., & Kim, K. W. (1999). The intramolecular photocyclization and photoreduction of 2-halo-N-pyridinylbenzamide. In CLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics (Vol. 2, pp. 346-347). [811461] Institute of Electrical and Electronics Engineers Inc.. https://doi.org/10.1109/CLEOPR.1999.811461
Song, Nam Woong ; Kim, Dongho ; Park, Yong Tae ; Jung, Chang Hee ; Kim, Kwang Wook. / The intramolecular photocyclization and photoreduction of 2-halo-N-pyridinylbenzamide. CLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics. Vol. 2 Institute of Electrical and Electronics Engineers Inc., 1999. pp. 346-347
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Song, NW, Kim, D, Park, YT, Jung, CH & Kim, KW 1999, The intramolecular photocyclization and photoreduction of 2-halo-N-pyridinylbenzamide. in CLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics. vol. 2, 811461, Institute of Electrical and Electronics Engineers Inc., pp. 346-347, 1999 Pacific Rim Conference on Lasers and Electro-Optics, CLEO/Pacific Rim 1999, Seoul, Korea, Republic of, 99/8/30. https://doi.org/10.1109/CLEOPR.1999.811461

The intramolecular photocyclization and photoreduction of 2-halo-N-pyridinylbenzamide. / Song, Nam Woong; Kim, Dongho; Park, Yong Tae; Jung, Chang Hee; Kim, Kwang Wook.

CLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics. Vol. 2 Institute of Electrical and Electronics Engineers Inc., 1999. p. 346-347 811461.

Research output: Chapter in Book/Report/Conference proceedingConference contribution

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AB - The intramolecular photocyclization of aryl halide has been investigated in relation to the synthetic method and the reaction mechanism. It is reported that heterocyclic molecular systems are formed from the photocyclization of haloarene tethered to arene by several linkages and a photohomolytic radical mechanism is involved in the photocyclization of N-phenylalkyl-2-halopyridinium and N-(2-halophenyl)alkyl pyridinium salts. In conjunction with the study of the heterocyclic ring formation, we observed that photoreaction of N-(2-halophenyl)pyridinecarboxamide in a basic medium produced an intramolecular photosubstitution product, 2-pyridinylbenzoxazole, instead of a photocyclization product, whereas photoreaction of 2-chloro-N-pyridinylbenzamide in a weak basic or neutral medium afforded an intramolecular photocyclization product, benzo[c]naphthyridinones. These reactions are straightforward and valuable for the syntheses of heterocyclic compounds such as benzoxazole and benzonaphthyridinone derivatives. Thus, it is desirable to develop the synthetic methods of the heterocyclic compounds and to clarify their reaction mechanisms. In this work, we have studied the photochemical reaction mechanism of 2-halo-N-pyridinylbenzamide by using a nanosecond laser flash photolysis technique.

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BT - CLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics

PB - Institute of Electrical and Electronics Engineers Inc.

ER -

Song NW, Kim D, Park YT, Jung CH, Kim KW. The intramolecular photocyclization and photoreduction of 2-halo-N-pyridinylbenzamide. In CLEO/Pacific Rim 1999 - Pacific Rim Conference on Lasers and Electro-Optics. Vol. 2. Institute of Electrical and Electronics Engineers Inc. 1999. p. 346-347. 811461 https://doi.org/10.1109/CLEOPR.1999.811461