ChemInform Abstract: Generation of 6-(Trifluoromethyl)-4,5-dihydro-2(3H)-pyridone and the Application to Synthesis of Some Fused Nitrogen Heterocycles Carrying a Trifluoromethyl Group on the Bridgehead Position via Radical Cyclization of Dihydropyridones.

Abstract Atropisomerism owing to hindered rotation about the N-aryl bond is observed in 4,5-diethyl-2,2,3-trimethyl-1-(o-trifluormethyl)phenyl-2,5-dihydro-1H-1,2,5-azasila-(2) and -azastanna-boroles (5). The compounds 2 and 5 are characterized by elemental analysis, mass spectra and 1H, 11B, 13 C, 29Si and119Sn NMR. The ortho-trifluoromethyl group serves as an additional NMR spectroscopic probe because of “through space” 19F-1H and 19F-13C spin spin coupling. Compound 5 is the first derivative of a 2,5-dihydro-1H-1,2,5-azastannaborol.

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ChemInform Abstract: Synthesis of Five-Membered Nitrogen Heterocycles Substituted with a Trifluoromethyl Group.

ChemInform ◽

10.1002/chin.198952162 ◽

1989 ◽

Vol 20 (52) ◽

Author(s):

K. QUINZE ◽

A. LAURENT ◽

P. MISON

Keyword(s):

Nitrogen Heterocycles ◽

Trifluoromethyl Group

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Evidence for a Radical Mechanism in Cu(II)-Promoted SnAP Reactions

Synlett ◽

10.1055/s-0037-1611670 ◽

2019 ◽

Vol 30 (04) ◽

pp. 464-470 ◽

Cited By ~ 2

Author(s):

Michael Luescher ◽

Jeffrey Bode

Keyword(s):

Nitrogen Heterocycles ◽

Radical Cyclization ◽

Bioactive Molecules ◽

Current Understanding ◽

Radical Mechanism ◽

Radical Trapping ◽

Wide Range ◽

Aldehydes And Ketones ◽

One Step ◽

Radical Clock

Saturated nitrogen heterocycles can be found with increasing abundance in bioactive molecules despite a limited number of methods to access these scaffolds. However, the coupling of recently introduced SnAP [tin (Sn) amine protocol] reagents with a wide range of aldehydes and ketones has proven to be a reliable, practical, and versatile one-step approach to saturated N-heterocycles. While effective, the lack of mechanistic understanding limits efforts to develop new catalytic and enantioselective variants. To distinguish between a polar or radical mechanism, we assessed Lewis and Brønsted acids, radical trapping experiments, and radical clock SnAP reagents reinforcing the current understanding of the SnAP protocol as a radical cyclization.

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ChemInform Abstract: Tributyltin Hydride-Mediated Radical Cyclization of Carbonyls to Form Functionalized Oxygen and Nitrogen Heterocycles.

ChemInform ◽

10.1002/chin.200243055 ◽

2010 ◽

Vol 33 (43) ◽

pp. no-no

Author(s):

Jon Bentley ◽

Paul A. Nilsson ◽

Andrew F. Parsons

Keyword(s):

Nitrogen Heterocycles ◽

Radical Cyclization ◽

Tributyltin Hydride

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Oxidation ofp-Aminophenols and Formal Radical Cyclization onto Benzene Rings: Formation of Benzo-Fused Nitrogen Heterocycles†

Organic Letters ◽

10.1021/ol047977j ◽

2005 ◽

Vol 7 (1) ◽

pp. 23-26 ◽

Cited By ~ 9

Author(s):

Stephen P. Fletcher ◽

Derrick L. J. Clive ◽

Jianbiao Peng ◽

David A. Wingert

Keyword(s):

Nitrogen Heterocycles ◽

Radical Cyclization ◽

Benzene Rings

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Conversion of Olefins into Five-membered Nitrogen Heterocycles by Radical Cyclization

Heterocycles ◽

10.3987/com-88-s141 ◽

1989 ◽

Vol 28 (2) ◽

pp. 1157 ◽

Cited By ~ 9

Author(s):

Derrick L. J. Clive ◽

Ali Y. Mohammed

Keyword(s):

Nitrogen Heterocycles ◽

Radical Cyclization

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First examples of intramolecular addition of primary amidyl radicals to olefins

Canadian Journal of Chemistry ◽

10.1139/v05-029 ◽

2005 ◽

Vol 83 (6-7) ◽

pp. 543-545 ◽

Cited By ~ 10

Author(s):

Philippe Gaudreault ◽

Christian Drouin ◽

Jean Lessard

Keyword(s):

Key Words ◽

Nitrogen Heterocycles ◽

Catalytic Amount ◽

Radical Cyclization ◽

Tributyltin Hydride

The first examples of intramolecular addition of primary amidyl radicals to olefins are described. Amidyl radicals were generated from N-(phenylthio)amides in refluxing benzene using a catalytic amount of 2,2′-azobis(isobutyronitrile) (5 mol%) and tributyltin hydride (~2.2 equiv.). The resulting yields of cyclic products ranged from 63% to 85%.Key words: radical cyclization, amidyl radicals, nitrogen heterocycles.

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