Ring-Fused 1,4-Dihydro[1,2,4]triazin-4-yls through Photocyclization

Halogen lamp irradiation of benzo[e][1,2,4]triazines 2[X] in CH2Cl2 solutions leads to planar ring-fused 1,4-dihydro[1,2,4]triazin-4-yl radicals 1 through a novel, potentially general, cyclization mechanism. The scope and efficiency of the method were established for unsubstituted and ortho-su...

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Veröffentlicht in:	Org. Lett 2020-05, Vol.22 (10), p.3835-3840
Hauptverfasser:	Bartos, Paulina, Young, Victor G, Kaszyński, Piotr
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Sprache:	eng
Schlagworte:	Chemistry Chemistry, Organic Physical Sciences Science & Technology
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container_end_page	3840
container_issue	10
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container_title	Org. Lett
container_volume	22
creator	Bartos, Paulina Young, Victor G Kaszyński, Piotr
description	Halogen lamp irradiation of benzo[e][1,2,4]triazines 2[X] in CH2Cl2 solutions leads to planar ring-fused 1,4-dihydro[1,2,4]triazin-4-yl radicals 1 through a novel, potentially general, cyclization mechanism. The scope and efficiency of the method were established for unsubstituted and ortho-substituted (X = NH2, Br, NO2) phenoxy, naphthyloxy, and quinolinoxy derivatives 2[X]. The regioselectivity of 2[X] photocyclization was rationalized with DFT computational methods. Radicals 1 were characterized by spectroscopic (UV–vis, EPR), electrochemical, and XRD methods.
doi_str_mv	10.1021/acs.orglett.0c01074
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Lett</addtitle><date>2020-05-15</date><risdate>2020</risdate><volume>22</volume><issue>10</issue><spage>3835</spage><epage>3840</epage><pages>3835-3840</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Halogen lamp irradiation of benzo[e][1,2,4]triazines 2[X] in CH2Cl2 solutions leads to planar ring-fused 1,4-dihydro[1,2,4]triazin-4-yl radicals 1 through a novel, potentially general, cyclization mechanism. The scope and efficiency of the method were established for unsubstituted and ortho-substituted (X = NH2, Br, NO2) phenoxy, naphthyloxy, and quinolinoxy derivatives 2[X]. The regioselectivity of 2[X] photocyclization was rationalized with DFT computational methods. 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title	Ring-Fused 1,4-Dihydro[1,2,4]triazin-4-yls through Photocyclization
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