A selective synthesis of β-isothiocyanato ketones through a Staudinger/aza-Wittig reaction of β-azido ketones

Fesenko, Anastasia A.; Dem’yachenko, Ekaterina A.; Федорова, Г. А.; Шуталев, А. Д.

doi:10.1007/s00706-012-0869-3

Cited by 14 publications

(7 citation statements)

References 38 publications

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“…The transformation of the azide group into an isothiocyanate was based on a procedure described for this conversion in solution. When PAO-N 3 is treated with triphenylphosphine, nitrogen is released due to the Staudinger reaction, and subsequent addition of carbon disulfide to the iminophosphorane-terminated intermediate surface yields PAO-NCS . The conversion of PAO-N 3 into PAO-NCS was observed by the appearance of the sulfur peak in the XPS survey scan and the presence of three carbon peaks in the XPS C 1s spectrum: C –C (285.0 eV), C –N (286.5 eV), and N C S (287.7 eV) (Figure ).…”

Section: Results and Discussionmentioning

confidence: 99%

“…When PAO-N 3 is treated with triphenylphosphine, nitrogen is released due to the Staudinger reaction, and subsequent addition of carbon disulfide to the iminophosphorane-terminated intermediate surface yields PAO-NCS. 44 The conversion of PAO-N 3 into PAO-NCS was observed by the appearance of the sulfur peak in the XPS survey scan and the presence of three carbon peaks in the XPS C 1s spectrum: C−C (285.0 eV), C−N (286.5 eV), and N CS (287.7 eV) (Figure 7). In a previous work, Lex and coworkers prepared isothiocyanate-terminated surfaces upon UV irradiation of thiocyanate-terminated surfaces.…”

Section: (See Figure Si-1 For Xps Data)mentioning

confidence: 99%

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Versatile (Bio)Functionalization of Bromo-Terminated Phosphonate-Modified Porous Aluminum Oxide

Debrassi

Roeven²,

Thijssen

et al. 2015

Langmuir

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Porous aluminum oxide (PAO) is a nanoporous material used for various (bio)technological applications, and tailoring its surface properties via covalent modification is a way to expand and refine its application. Specific and complex chemical modification of the PAO surface requires a stepwise approach in which a secondary reaction on a stable initial modification is necessary to achieve the desired terminal molecular architecture and reactivity. We here show that the straightforward initial modification of the bare PAO surface with bromo-terminated phosphonic acid allows for the subsequent preparation of PAO with a wide scope of terminal reactive groups, making it suitable for (bio)functionalization. Starting from the initial bromo-terminated PAO, we prepared PAO surfaces presenting various terminal functional groups, such as azide, alkyne, alkene, thiol, isothiocyanate, and N-hydroxysuccinimide (NHS). We also show that this wide scope of easily accessible tailored reactive PAO surfaces can be used for subsequent modification with (bio)molecules, including carbohydrate derivatives and fluorescently labeled proteins.

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Section: Results and Discussionmentioning

confidence: 99%

Section: (See Figure Si-1 For Xps Data)mentioning

confidence: 99%

Versatile (Bio)Functionalization of Bromo-Terminated Phosphonate-Modified Porous Aluminum Oxide

Debrassi

Roeven²,

Thijssen

et al. 2015

Langmuir

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“…The 1 H NMR spectra of 4a-k in DMSO-d6 show a long-range coupling between the (thio)amide N(2)H and N(4)H protons ( 4 J = 2.0-2.5 Hz) that indicates their one-plane W-shaped arrangement. Similar long-range couplings are characteristic of N-unsubstituted (thio)ureide-containing heterocycles, e.g., 2,3,4,5-tetrahydroand 2,3-dihydro-1H-1,3-diazepin-2-ones [57][58][59][60][61], hexahydro-and 1,2,3,4-tetrahydropyrimidine-2thiones/ones [57][58][59][60][61][62][63][64][65][66][67][68], 2,4,5,6-tetrahydro-3H-1,2,4-triazepine-3-thiones/ones [18,19,42]. Two alternative procedures were developed for preparation of 1-alkyl-substituted 1,2,4-triazepane-3-thiones/ones.…”

Section: Resultsmentioning

confidence: 80%

A General Stereoselective Approach to 1,2,4-Triazepane-3-thiones/ones via Reduction or Reductive Alkylation of 2,4,5,6-Tetrahydro-3H-1,2,4-triazepine-3-thiones/ones

Fesenko

Шуталев

2018

22nd International Electronic Conference on Synthetic Organic Chemistry

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A general stereoselective approach to previously unknown 1,2,4-triazepane-3-thiones/ones based on reduction or reductive alkylation of readily available 2,4,5,6-tetrahydro-3H-1,2,4-triazepine- 3-thiones/ones has been developed. The approach involved treatment of tetrahydrotriazepines with sodium cyanoborohydride in MeOH at pH 3 or with sodium borohydride and excess of carboxylic acid in tetrahydrofuran to give 1-unsubstituted or 1-alkyl-substituted 1,2,4-triazepane-3- thiones/ones, respectively. The latter were also prepared by reaction of 1-unsubstituted 1,2,4- triazepane-3-thiones/ones with sodium cyanoborohydride and aldehyde in MeOH in the presence of AcOH.

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“…The starting material, 4-isothiocyanatobutan-2-one ( 10 ), was prepared according to our regioselective procedure 22 by the addition of HN 3 to methyl vinyl ketone ( 8 ) followed by the reaction of the obtained azidoketone 9 with CS 2 and PPh 3 in 40% overall yield after vacuum distillation ( Scheme 2 ).…”

Section: Resultsmentioning

confidence: 99%

Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation

et al. 2022

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Unprecedented self-assembly of a novel 14-membered cyclic bis-thiosemicarbazone or/and a 28-membered cyclic tetrakis-thiosemicarbazone upon acid-promoted cyclooligomerization of 4-(4-thiosemicarbazido)butan-2-one hydrazone has been discovered. A thorough study of the influence of various factors on the direction of macrocyclization provided the optimal conditions for the highly selective formation of each of the macrocycles in excellent yields. Plausible pathways for macrocyclizations have been discussed. The macrocycle precursor was prepared by the reaction of readily available 4-isothiocyanatobutan-2-one with an excess of hydrazine.

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A selective synthesis of β-isothiocyanato ketones through a Staudinger/aza-Wittig reaction of β-azido ketones

Cited by 14 publications

References 38 publications

Versatile (Bio)Functionalization of Bromo-Terminated Phosphonate-Modified Porous Aluminum Oxide

Versatile (Bio)Functionalization of Bromo-Terminated Phosphonate-Modified Porous Aluminum Oxide

A General Stereoselective Approach to 1,2,4-Triazepane-3-thiones/ones via Reduction or Reductive Alkylation of 2,4,5,6-Tetrahydro-3H-1,2,4-triazepine-3-thiones/ones

Different Modes of Acid-Promoted Cyclooligomerization of 4-(4-Thiosemicarbazido)butan-2-one Hydrazone: 14-Membered versus 28-Membered Polyazamacrocycle Formation

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