Improvements in or relating to the manufacture of heterocyclic compounds
Benziminazole glycosides of the formula where R and R1 are hydrogen, methyl or ethyl and R2 is a residue of the formula n being 2 and R3 being -CH2OR4 or -CHOR4 -CH2OR4 or else n being 3 and R3 being -H or -CH2OR4 (R4=acyl), are prepared by reacting the silver derivative of the benziminazole with...
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creator | STURGEON BENNETT PETROW VLADIMIR MAMALIS PATRICK |
description | Benziminazole glycosides of the formula where R and R1 are hydrogen, methyl or ethyl and R2 is a residue of the formula n being 2 and R3 being -CH2OR4 or -CHOR4 -CH2OR4 or else n being 3 and R3 being -H or -CH2OR4 (R4=acyl), are prepared by reacting the silver derivative of the benziminazole with the halogen derivative of the appropriate acylated sugar; the product may, if desired, be deacylated. The reaction is carried in a dry inert solvent, e.g. benzene, toluene or xylene dried over sodium. The materials are heated to 150 DEG C. or reflux temperature for 1/2 -5 hours. The product may have the a - or b -configuration or may be a mixture of both isomers. It is preferably isolated as the picrate. In the examples silver 5 : 6-dimethylbenziminazole is reacted with acetobromo-L-arabinose, acetobromoglucose, acetobromoribose and bromo-tribenzoyl-D-ribose, silver benzininazole with acetobromoribose and acetobromo-D-xylose, silver 5-methylbenziminazole with acetobromarabinose and silver 4 : 5-dimethylbenziminazole with acetobromoglucose. According to the Provisional Specification R2 is a residue of the formula -CHOH(CHOH)n CH2OH or the corresponding furano, pyrano or open-chain sugar residues, n being not greater than 4. Such residue is preferably acetylated during the reaction. The sugar may be a hexose pentose or methylpentose. Reference has been directed by the Comptroller to Specification 682,960. |
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The reaction is carried in a dry inert solvent, e.g. benzene, toluene or xylene dried over sodium. The materials are heated to 150 DEG C. or reflux temperature for 1/2 -5 hours. The product may have the a - or b -configuration or may be a mixture of both isomers. It is preferably isolated as the picrate. In the examples silver 5 : 6-dimethylbenziminazole is reacted with acetobromo-L-arabinose, acetobromoglucose, acetobromoribose and bromo-tribenzoyl-D-ribose, silver benzininazole with acetobromoribose and acetobromo-D-xylose, silver 5-methylbenziminazole with acetobromarabinose and silver 4 : 5-dimethylbenziminazole with acetobromoglucose. According to the Provisional Specification R2 is a residue of the formula -CHOH(CHOH)n CH2OH or the corresponding furano, pyrano or open-chain sugar residues, n being not greater than 4. Such residue is preferably acetylated during the reaction. The sugar may be a hexose pentose or methylpentose. Reference has been directed by the Comptroller to Specification 682,960.</description><language>eng</language><subject>CHEMISTRY ; DERIVATIVES THEREOF ; METALLURGY ; NUCLEIC ACIDS ; NUCLEOSIDES ; NUCLEOTIDES ; ORGANIC CHEMISTRY ; SUGARS</subject><creationdate>1953</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19530909&DB=EPODOC&CC=GB&NR=696952A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,776,881,25543,76293</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19530909&DB=EPODOC&CC=GB&NR=696952A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>STURGEON BENNETT</creatorcontrib><creatorcontrib>PETROW VLADIMIR</creatorcontrib><creatorcontrib>MAMALIS PATRICK</creatorcontrib><title>Improvements in or relating to the manufacture of heterocyclic compounds</title><description>Benziminazole glycosides of the formula <FORM:0696952/IV (b)/1> where R and R1 are hydrogen, methyl or ethyl and R2 is a residue of the formula <FORM:0696952/IV (b)/2> n being 2 and R3 being -CH2OR4 or -CHOR4 -CH2OR4 or else n being 3 and R3 being -H or -CH2OR4 (R4=acyl), are prepared by reacting the silver derivative of the benziminazole with the halogen derivative of the appropriate acylated sugar; the product may, if desired, be deacylated. The reaction is carried in a dry inert solvent, e.g. benzene, toluene or xylene dried over sodium. The materials are heated to 150 DEG C. or reflux temperature for 1/2 -5 hours. The product may have the a - or b -configuration or may be a mixture of both isomers. It is preferably isolated as the picrate. In the examples silver 5 : 6-dimethylbenziminazole is reacted with acetobromo-L-arabinose, acetobromoglucose, acetobromoribose and bromo-tribenzoyl-D-ribose, silver benzininazole with acetobromoribose and acetobromo-D-xylose, silver 5-methylbenziminazole with acetobromarabinose and silver 4 : 5-dimethylbenziminazole with acetobromoglucose. According to the Provisional Specification R2 is a residue of the formula -CHOH(CHOH)n CH2OH or the corresponding furano, pyrano or open-chain sugar residues, n being not greater than 4. Such residue is preferably acetylated during the reaction. The sugar may be a hexose pentose or methylpentose. Reference has been directed by the Comptroller to Specification 682,960.</description><subject>CHEMISTRY</subject><subject>DERIVATIVES THEREOF</subject><subject>METALLURGY</subject><subject>NUCLEIC ACIDS</subject><subject>NUCLEOSIDES</subject><subject>NUCLEOTIDES</subject><subject>ORGANIC CHEMISTRY</subject><subject>SUGARS</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1953</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNqFyjEKAjEQBdA0FqJeQeYCNooLW7qirr39EuKPG0hmQjIRvL2NvdVr3tKM95SLvJHAWikwSaGCaDXwi1RIZ1Cy3Lx12gpIPM1QFHEfF4MjJylL42ddm4W3sWLzc2W218vjPO6QZULN1oGh023o-q4_7k-Hv-ELriAzpA</recordid><startdate>19530909</startdate><enddate>19530909</enddate><creator>STURGEON BENNETT</creator><creator>PETROW VLADIMIR</creator><creator>MAMALIS PATRICK</creator><scope>EVB</scope></search><sort><creationdate>19530909</creationdate><title>Improvements in or relating to the manufacture of heterocyclic compounds</title><author>STURGEON BENNETT ; PETROW VLADIMIR ; MAMALIS PATRICK</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_GB696952A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>1953</creationdate><topic>CHEMISTRY</topic><topic>DERIVATIVES THEREOF</topic><topic>METALLURGY</topic><topic>NUCLEIC ACIDS</topic><topic>NUCLEOSIDES</topic><topic>NUCLEOTIDES</topic><topic>ORGANIC CHEMISTRY</topic><topic>SUGARS</topic><toplevel>online_resources</toplevel><creatorcontrib>STURGEON BENNETT</creatorcontrib><creatorcontrib>PETROW VLADIMIR</creatorcontrib><creatorcontrib>MAMALIS PATRICK</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>STURGEON BENNETT</au><au>PETROW VLADIMIR</au><au>MAMALIS PATRICK</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Improvements in or relating to the manufacture of heterocyclic compounds</title><date>1953-09-09</date><risdate>1953</risdate><abstract>Benziminazole glycosides of the formula <FORM:0696952/IV (b)/1> where R and R1 are hydrogen, methyl or ethyl and R2 is a residue of the formula <FORM:0696952/IV (b)/2> n being 2 and R3 being -CH2OR4 or -CHOR4 -CH2OR4 or else n being 3 and R3 being -H or -CH2OR4 (R4=acyl), are prepared by reacting the silver derivative of the benziminazole with the halogen derivative of the appropriate acylated sugar; the product may, if desired, be deacylated. The reaction is carried in a dry inert solvent, e.g. benzene, toluene or xylene dried over sodium. The materials are heated to 150 DEG C. or reflux temperature for 1/2 -5 hours. The product may have the a - or b -configuration or may be a mixture of both isomers. It is preferably isolated as the picrate. In the examples silver 5 : 6-dimethylbenziminazole is reacted with acetobromo-L-arabinose, acetobromoglucose, acetobromoribose and bromo-tribenzoyl-D-ribose, silver benzininazole with acetobromoribose and acetobromo-D-xylose, silver 5-methylbenziminazole with acetobromarabinose and silver 4 : 5-dimethylbenziminazole with acetobromoglucose. According to the Provisional Specification R2 is a residue of the formula -CHOH(CHOH)n CH2OH or the corresponding furano, pyrano or open-chain sugar residues, n being not greater than 4. Such residue is preferably acetylated during the reaction. The sugar may be a hexose pentose or methylpentose. Reference has been directed by the Comptroller to Specification 682,960.</abstract><oa>free_for_read</oa></addata></record> |
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subjects | CHEMISTRY DERIVATIVES THEREOF METALLURGY NUCLEIC ACIDS NUCLEOSIDES NUCLEOTIDES ORGANIC CHEMISTRY SUGARS |
title | Improvements in or relating to the manufacture of heterocyclic compounds |
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