N-Glykosyl-Derivate. Teil XIII. Der nachträgliche ausbau des aglykons. Synthese von N-Glykosyl-Derivaten des 2-amino-thiazols, 2-amino-1,3,4-thiadiazols und 5-amino-1,2,3,4-thiatriazols

R. Bognár, L. Somogyi, L. Szilágyi, Z. Györgydeák

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13 Citations (Scopus)

Abstract

Some new N-d-glucosyl derivatives have been obtained from simpler d-glucosylamine derivatives by further substitution of the aglycon groups. Condensation of (tetra-O-acetyl-d-glucopyranosyl)thiourea (1) with 1-chloro-2-propanone gave 4 methyl-2-(tetra-O-acetyl-d-glucopyranosylamino)thiazole (2) and, with 2-bromo-acetophenone, the corresponding 4-phenyl analogue (4). Treatment of 4-(tetra-O-acetyl-d-glucopyranosyl)thiosemicarbazide (5) with triethyl orthoformate gave 2-(tetra-O-acetyl-d-glucopyranosylamino)-1,3,4-thiadiazole (6).5-(Tetra-O-acetyl-d-glucopyranosylamino)-1,2,3,4-thiatriazole (9) was prepared by the action of nitrous acid on 5 as well as by the action of azoimide on tetra-O-acetyl-d-glucopyranosyl isothiocyanate (8). The addition of p-chloroaniline to 8 or p-chlorophenyl isothiocyanate to tetra-O-acetyl-d-glucopyranosylamine (11) gave N-(p-chlorophenyl)N′-tetra-O-acetyl-d-glucopyranosyl)thiourea (12). The tetraacetates of the new d-glucosylamine derivatives were deacetylated. 1-[(Tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiosemicarbazide, (14) was synthesised from 8 by treatment with thiosemicarbazide, and 1,5-bis[(tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiocarbonohydrazide (15) was obtained from 8 and thiocarbohydrazide. Preparation of some new (O-acetyl-d-glucosyl)thiosemicarbazones is described, and physical and infrared data of these compounds are included.

Original languageGerman
Pages (from-to)320-328
Number of pages9
JournalCarbohydrate Research
Volume5
Issue number3
Publication statusPublished - Nov 1967

ASJC Scopus subject areas

  • Organic Chemistry
  • Molecular Biology
  • Biochemistry

Cite this

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title = "N-Glykosyl-Derivate. Teil XIII. Der nachtr{\"a}gliche ausbau des aglykons. Synthese von N-Glykosyl-Derivaten des 2-amino-thiazols, 2-amino-1,3,4-thiadiazols und 5-amino-1,2,3,4-thiatriazols",
abstract = "Some new N-d-glucosyl derivatives have been obtained from simpler d-glucosylamine derivatives by further substitution of the aglycon groups. Condensation of (tetra-O-acetyl-d-glucopyranosyl)thiourea (1) with 1-chloro-2-propanone gave 4 methyl-2-(tetra-O-acetyl-d-glucopyranosylamino)thiazole (2) and, with 2-bromo-acetophenone, the corresponding 4-phenyl analogue (4). Treatment of 4-(tetra-O-acetyl-d-glucopyranosyl)thiosemicarbazide (5) with triethyl orthoformate gave 2-(tetra-O-acetyl-d-glucopyranosylamino)-1,3,4-thiadiazole (6).5-(Tetra-O-acetyl-d-glucopyranosylamino)-1,2,3,4-thiatriazole (9) was prepared by the action of nitrous acid on 5 as well as by the action of azoimide on tetra-O-acetyl-d-glucopyranosyl isothiocyanate (8). The addition of p-chloroaniline to 8 or p-chlorophenyl isothiocyanate to tetra-O-acetyl-d-glucopyranosylamine (11) gave N-(p-chlorophenyl)N′-tetra-O-acetyl-d-glucopyranosyl)thiourea (12). The tetraacetates of the new d-glucosylamine derivatives were deacetylated. 1-[(Tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiosemicarbazide, (14) was synthesised from 8 by treatment with thiosemicarbazide, and 1,5-bis[(tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiocarbonohydrazide (15) was obtained from 8 and thiocarbohydrazide. Preparation of some new (O-acetyl-d-glucosyl)thiosemicarbazones is described, and physical and infrared data of these compounds are included.",
author = "R. Bogn{\'a}r and L. Somogyi and L. Szil{\'a}gyi and Z. Gy{\"o}rgyde{\'a}k",
year = "1967",
month = "11",
language = "German",
volume = "5",
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journal = "Carbohydrate Research",
issn = "0008-6215",
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T1 - N-Glykosyl-Derivate. Teil XIII. Der nachträgliche ausbau des aglykons. Synthese von N-Glykosyl-Derivaten des 2-amino-thiazols, 2-amino-1,3,4-thiadiazols und 5-amino-1,2,3,4-thiatriazols

AU - Bognár, R.

AU - Somogyi, L.

AU - Szilágyi, L.

AU - Györgydeák, Z.

PY - 1967/11

Y1 - 1967/11

N2 - Some new N-d-glucosyl derivatives have been obtained from simpler d-glucosylamine derivatives by further substitution of the aglycon groups. Condensation of (tetra-O-acetyl-d-glucopyranosyl)thiourea (1) with 1-chloro-2-propanone gave 4 methyl-2-(tetra-O-acetyl-d-glucopyranosylamino)thiazole (2) and, with 2-bromo-acetophenone, the corresponding 4-phenyl analogue (4). Treatment of 4-(tetra-O-acetyl-d-glucopyranosyl)thiosemicarbazide (5) with triethyl orthoformate gave 2-(tetra-O-acetyl-d-glucopyranosylamino)-1,3,4-thiadiazole (6).5-(Tetra-O-acetyl-d-glucopyranosylamino)-1,2,3,4-thiatriazole (9) was prepared by the action of nitrous acid on 5 as well as by the action of azoimide on tetra-O-acetyl-d-glucopyranosyl isothiocyanate (8). The addition of p-chloroaniline to 8 or p-chlorophenyl isothiocyanate to tetra-O-acetyl-d-glucopyranosylamine (11) gave N-(p-chlorophenyl)N′-tetra-O-acetyl-d-glucopyranosyl)thiourea (12). The tetraacetates of the new d-glucosylamine derivatives were deacetylated. 1-[(Tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiosemicarbazide, (14) was synthesised from 8 by treatment with thiosemicarbazide, and 1,5-bis[(tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiocarbonohydrazide (15) was obtained from 8 and thiocarbohydrazide. Preparation of some new (O-acetyl-d-glucosyl)thiosemicarbazones is described, and physical and infrared data of these compounds are included.

AB - Some new N-d-glucosyl derivatives have been obtained from simpler d-glucosylamine derivatives by further substitution of the aglycon groups. Condensation of (tetra-O-acetyl-d-glucopyranosyl)thiourea (1) with 1-chloro-2-propanone gave 4 methyl-2-(tetra-O-acetyl-d-glucopyranosylamino)thiazole (2) and, with 2-bromo-acetophenone, the corresponding 4-phenyl analogue (4). Treatment of 4-(tetra-O-acetyl-d-glucopyranosyl)thiosemicarbazide (5) with triethyl orthoformate gave 2-(tetra-O-acetyl-d-glucopyranosylamino)-1,3,4-thiadiazole (6).5-(Tetra-O-acetyl-d-glucopyranosylamino)-1,2,3,4-thiatriazole (9) was prepared by the action of nitrous acid on 5 as well as by the action of azoimide on tetra-O-acetyl-d-glucopyranosyl isothiocyanate (8). The addition of p-chloroaniline to 8 or p-chlorophenyl isothiocyanate to tetra-O-acetyl-d-glucopyranosylamine (11) gave N-(p-chlorophenyl)N′-tetra-O-acetyl-d-glucopyranosyl)thiourea (12). The tetraacetates of the new d-glucosylamine derivatives were deacetylated. 1-[(Tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiosemicarbazide, (14) was synthesised from 8 by treatment with thiosemicarbazide, and 1,5-bis[(tetra-O-acetyl-d-glucopyranosyl)thiocarbamoyl]thiocarbonohydrazide (15) was obtained from 8 and thiocarbohydrazide. Preparation of some new (O-acetyl-d-glucosyl)thiosemicarbazones is described, and physical and infrared data of these compounds are included.

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