GB690119A - Improvements in or relating to the manufacture of heterocyclic compounds - Google Patents

Improvements in or relating to the manufacture of heterocyclic compounds

Info

Publication number
GB690119A
GB690119A GB1761050A GB1761050A GB690119A GB 690119 A GB690119 A GB 690119A GB 1761050 A GB1761050 A GB 1761050A GB 1761050 A GB1761050 A GB 1761050A GB 690119 A GB690119 A GB 690119A
Authority
GB
United Kingdom
Prior art keywords
picrate
benziminazole
tetracetylglucoside
methylbenziminazole
dimethylbenziminazole
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB1761050A
Inventor
Patrick Mamalis
Vladimir Petrow
Bennett Sturgeon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB1761050A priority Critical patent/GB690119A/en
Publication of GB690119A publication Critical patent/GB690119A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/052Imidazole radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Saccharide Compounds (AREA)

Abstract

Benziminazole glycosides of the formula <FORM:0690119/IV (b)/1> where R and R1 are hydrogen, methyl or ethyl and R2 is a residue of the formula <FORM:0690119/IV (b)/2> n being 2 and R3 being -CH2OH or -CHOH-CH2OH or else n being 3 and R3 being -H or -CH2OH, are prepared by reacting the R,R1,R2-substituted o-phenylene diamine with an alkyl orthoformate to give the isoformanilide and ring-closing the latter with acid, e.g. hydrochloric or picric. The first step is preferably carried out by refluxing with ethyl orthoformate in an inert solvent, e.g. alcohol, ethyl acetate or benzene. The hydroxyl groups may be protected by acetylation before the reaction and the final product then deacetylated. Alternatively the terminal hydroxyl group may be converted into the trityl, benzyl, toluenesulphonyl or diphenylphosphoryl derivative; some or all of the remaining hydroxyl groups may then be protected by way of the acetyl, isopropylidene or benzylidene derivatives. In the examples: (1) o-nitraniline tetracetyl-d-glucoside is catalytically reduced to the diamine derivative and reacted with ethyl orthoformate to give N-ethoxymethylene-o-phenylene diamine N1-tetracetylglucoside; ring-closure yields benziminazole - d - tetracetylglucoside (picrate described), hydrolysed to the hydrochloride of benziminazole-1b -d-glucopyranoxide; the free base is formed by passage of the hydrochloride through a basic ion-exchange resin; (2) o-nitraniline is condensed with d-xylose to give the xyloside and converted into o-nitraniline-triacetylxyloside; treatment as above gives benziminazole-triacetylxyloside (via picrate) and benziminazole-1b -d-xylopyranoside (via hydrochloride); (3) 3-nitro-p-toluidine condensed with d-xylose gives a mixture of isomeric xylosides; these are acetylated and converted as above into 5-methylbenziminazole - triacetyl - xyloside (via picrate) and 5-methylbenziminazole - 1 - d - xylopyranoside; (4) 3-nitro-p-toluidine similarly gives a mixture of glucosides separated after acetylation and reduced to the diamine derivative; treatment as above gives 5-methylbenziminazole-tetracetylglucoside (via picrate) and 5-methylbenziminazole - 1 - d - glucopyranoside; (5) 5 - nitro - o - xylidine is condensed with glucose, acetylated, separated into isomers and reduced; treatment as above gives 5 : 6-dimethylbenziminazole - tetracetylglucoside and 5 : 6 - dimethylbenziminazole - 1b - d - glucopyranoside; (6) there are similarly prepared 5 - nitro - o - xylidine - triacetylarabinoside (2 isomers), 5 : 6 - dimethylbenziminazoletriacetylarabinoside (via picrate) and 5 : 6-dimethylbenziminazole - 1a - l - arabopyranoside (forms picrate); (7) 5 : 6-dimethylbenziminazole - 1b - d - ribopyranoside is similarly prepared (as hydrochloride). According to the Provisional Specification R and R1 are hydrogen or an alkyl grouping of molecular weight not exceeding 43 and R2 is a sugar residue of the formula -CHOH-(CHOH)n-CH2OH, n being not greater than 4; R2 may be in the furano, pyrano or open chain form of the sugar, and may be derived from a pentose or hexose. Reference has been directed by the Comptroller to Specification 682,960.
GB1761050A 1950-07-13 1950-07-13 Improvements in or relating to the manufacture of heterocyclic compounds Expired GB690119A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1761050A GB690119A (en) 1950-07-13 1950-07-13 Improvements in or relating to the manufacture of heterocyclic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1761050A GB690119A (en) 1950-07-13 1950-07-13 Improvements in or relating to the manufacture of heterocyclic compounds

Publications (1)

Publication Number Publication Date
GB690119A true GB690119A (en) 1953-04-15

Family

ID=10098153

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1761050A Expired GB690119A (en) 1950-07-13 1950-07-13 Improvements in or relating to the manufacture of heterocyclic compounds

Country Status (1)

Country Link
GB (1) GB690119A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001517674A (en) * 1997-09-22 2001-10-09 アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー Pentopyranosyl nucleosides, their production and use

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001517674A (en) * 1997-09-22 2001-10-09 アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー Pentopyranosyl nucleosides, their production and use
JP2001517676A (en) * 1997-09-22 2001-10-09 アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー Use of pentopyranosyl nucleosides for making electronic components and pentopyranosyl nucleoside conjugates
JP2001517675A (en) * 1997-09-22 2001-10-09 アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー Method for producing pentopyranosyl nucleoside
JP4674965B2 (en) * 1997-09-22 2011-04-20 ナノジェン・レコグノミクス・ゲーエムベーハー Use of pentopyranosyl nucleosides to produce electronic components and pentopyranosyl nucleoside conjugates
JP4674964B2 (en) * 1997-09-22 2011-04-20 ナノジェン・レコグノミクス・ゲーエムベーハー Pentopyranosyl nucleoside, its manufacture and use

Similar Documents

Publication Publication Date Title
Hasegawa et al. The behavior of some aldoses with 2, 2-dimethoxypropane-N, N-dimethylformamide-p-toluenesulfonic acid: I. At room temperature (≈ 25°)
NONAKA et al. Tannins and related compounds. LXXXV.: Structures of novel C-glycosidic ellagitannins, grandinin and pterocarinins A and B
Wei et al. Antiinflammatory triterpenoid saponins from the seeds of Aesculus chinensis
Seto et al. Sesquiterpene lactones from Ixeris dentata Nakai
Libnow et al. Synthesis of indirubin-N′-glycosides and their anti-proliferative activity against human cancer cell lines
Nana et al. Ceramides and cytotoxic constituents from Ficus glumosa Del.(Moraceae)
Yamamura et al. The Daphniphyllum Alkaloids
Prelog et al. The chemistry of Solanum and Veratrum alkaloids
NO301277B1 (en) 4-deoxy-4-epipodophyllotoxin derivative or pharmaceutically acceptable salt thereof, pharmaceutical compositions containing them, and use thereof
Nohara et al. Study on the constituents of Paris quadriforia L.
Lee et al. Sesquiterpenes from Syneilesis palmata and their cytotoxicity against human cancer cell lines in vitro
Shen et al. New furans from Cirsium chlorolepis
US3471470A (en) Novel derivatives of desglucohellebrin
Ma et al. Isosteroidal alkaloids from Fritillaria verticillata Willd. and their NMR spectroscopic characteristics
GB690119A (en) Improvements in or relating to the manufacture of heterocyclic compounds
Driller et al. Synthesis of 6 H-indolo [2, 3-b] quinoxaline-N-glycosides and their cytotoxic activity against human ceratinocytes (HaCaT)
Zhao et al. Three new triterpene saponins from the seeds of Aesculus chinensis
IKEHARA et al. Studies of nucleosides and nucleotides. XLIX. Synthesis of 8-fluoroadenosine
NAGUMO et al. New glucosides of a 4-hydroxy-5-methylcoumarin and a dihydro-α-pyrone from Gerbera jamesonii hybrida
PL124710B1 (en) Process for preparing esters of antibiotics from polyene macrolids group and their n-substituted derivatives
Umezawa et al. Studies on antibiotics and related substances. VII. The structure of kanamycin
Heard et al. Conversion of acyclic carbohydrates to tetrahydrofuran derivatives. Deamination of 1-amino-1-deoxypentitols
Venkannababu et al. Regulosides A–C: glycosphingolipids from the starfish Pentaceraster regulus
Lichtenthaler et al. Sugar Enolones, VII. Synthesis and γ‐Pyrone Formation of α, β‐Unsaturated Hexopyranosid‐4‐uloses
Cheng et al. Diterpene glycosides from Senecio rufus