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1 article(s) from Clem, Brittany S.

Synthesis of purines and adenines containing the hexafluoroisopropyl group

Viacheslav Petrov,
Rebecca J. Dooley,
Alexander A. Marchione,
Elizabeth L. Diaz,
Brittany S. Clem and
William Marshall

Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224

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Graphical Abstract

Scheme 1: Reaction of purine (2) with tetrakis(trifluoromethyl)-1,3-dithietane (1).

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Figure 1: Crystal structure of 2a, with the thermal ellipsoids drawn at 30% probability.

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Scheme 2: Reaction of 4-azabenzimidazole (3) with tetrakis(trifluoromethyl)-1,3-dithietane (1).

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Scheme 3: Reaction of 5-azabenzimidazole (4) with 1.

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Scheme 4: Reaction of adenine (5) and 2-fluoroadenine (6) with tetrakis(trifluoromethyl)-1,3-dithietane (1).

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Scheme 5: Reaction of theophylline (7) with tetrakis(trifluoromethyl)-1,3-dithietane (1).

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Figure 2: Crystal structure of 7a, with the thermal ellipsoids drawn at 30% probability.

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Scheme 6: Probable mechanism of the reaction of tetrakis(trifluoromethyl)-1,3-dithietane (1) with compounds 2–...

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Figure 3: Top: ¹⁹F NMR spectra of 3a acquired over a sample temperature range of 223–373 K. Left: Fitted plot...

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Figure 4: DFT-optimized structures of the two rotamers of 3a. Left: Lower-energy rotamer. Right: Higher-energ...

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Published 11 Nov 2020

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