PRODUCTION OF 1-POSITION SUBSTITUTED PYRROLE-3-CARBOXYLIC ACID DERIVATIVE
PROBLEM TO BE SOLVED: To obtain a pyrrole-3-carboxylic acid derivative useful as a medicine, its synthetic raw material and its intermediate simply in a short time in high yield by using an N-substituted formyl-glycine as a raw material. SOLUTION: A compound of formula I (R1 is an alkyl, an aralkyl...
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| creator | SHIBATA MAKOTO IMOTO MASAHIRO MIZUNO AKIRA IWAMORI CHIE |
| description | PROBLEM TO BE SOLVED: To obtain a pyrrole-3-carboxylic acid derivative useful as a medicine, its synthetic raw material and its intermediate simply in a short time in high yield by using an N-substituted formyl-glycine as a raw material. SOLUTION: A compound of formula I (R1 is an alkyl, an aralkyl or an aryl) is reacted with a compound of the formula, HC≡C-COOR2 (R2 is an alkyl, an aralkyl or an aryl) and an acid anhydride (e.g. acetic anhydride) at 80 deg.C to a reflux temperature for 4-24 hours with stirring to give a 1-position substituted pyrrole-3-carboxylic acid derivative of formula II. The compound of formula I in an amount of 1mol is reacted with >=1mol of the acid anhydride and 1-5mols of the compound of the formula, HC≡C-COOR2 . Since the reaction is not a substitution reaction on the pyrrole ring, production of pyrrole-2- carboxylic acid derivative as a by-production will not occur and a complicated separating process is not required. Since a dangerous reagent is not used, procedures are simple and reaction processed are a few and a time required for the synthesis can be shortened. |
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SOLUTION: A compound of formula I (R1 is an alkyl, an aralkyl or an aryl) is reacted with a compound of the formula, HC≡C-COOR2 (R2 is an alkyl, an aralkyl or an aryl) and an acid anhydride (e.g. acetic anhydride) at 80 deg.C to a reflux temperature for 4-24 hours with stirring to give a 1-position substituted pyrrole-3-carboxylic acid derivative of formula II. The compound of formula I in an amount of 1mol is reacted with >=1mol of the acid anhydride and 1-5mols of the compound of the formula, HC≡C-COOR2 . Since the reaction is not a substitution reaction on the pyrrole ring, production of pyrrole-2- carboxylic acid derivative as a by-production will not occur and a complicated separating process is not required. Since a dangerous reagent is not used, procedures are simple and reaction processed are a few and a time required for the synthesis can be shortened.</description><edition>6</edition><language>eng</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; HUMAN NECESSITIES ; HYGIENE ; MEDICAL OR VETERINARY SCIENCE ; METALLURGY ; ORGANIC CHEMISTRY ; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES ; SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS</subject><creationdate>1997</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=19970715&DB=EPODOC&CC=JP&NR=H09183765A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19970715&DB=EPODOC&CC=JP&NR=H09183765A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>SHIBATA MAKOTO</creatorcontrib><creatorcontrib>IMOTO MASAHIRO</creatorcontrib><creatorcontrib>MIZUNO AKIRA</creatorcontrib><creatorcontrib>IWAMORI CHIE</creatorcontrib><title>PRODUCTION OF 1-POSITION SUBSTITUTED PYRROLE-3-CARBOXYLIC ACID DERIVATIVE</title><description>PROBLEM TO BE SOLVED: To obtain a pyrrole-3-carboxylic acid derivative useful as a medicine, its synthetic raw material and its intermediate simply in a short time in high yield by using an N-substituted formyl-glycine as a raw material. SOLUTION: A compound of formula I (R1 is an alkyl, an aralkyl or an aryl) is reacted with a compound of the formula, HC≡C-COOR2 (R2 is an alkyl, an aralkyl or an aryl) and an acid anhydride (e.g. acetic anhydride) at 80 deg.C to a reflux temperature for 4-24 hours with stirring to give a 1-position substituted pyrrole-3-carboxylic acid derivative of formula II. The compound of formula I in an amount of 1mol is reacted with >=1mol of the acid anhydride and 1-5mols of the compound of the formula, HC≡C-COOR2 . Since the reaction is not a substitution reaction on the pyrrole ring, production of pyrrole-2- carboxylic acid derivative as a by-production will not occur and a complicated separating process is not required. 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SOLUTION: A compound of formula I (R1 is an alkyl, an aralkyl or an aryl) is reacted with a compound of the formula, HC≡C-COOR2 (R2 is an alkyl, an aralkyl or an aryl) and an acid anhydride (e.g. acetic anhydride) at 80 deg.C to a reflux temperature for 4-24 hours with stirring to give a 1-position substituted pyrrole-3-carboxylic acid derivative of formula II. The compound of formula I in an amount of 1mol is reacted with >=1mol of the acid anhydride and 1-5mols of the compound of the formula, HC≡C-COOR2 . Since the reaction is not a substitution reaction on the pyrrole ring, production of pyrrole-2- carboxylic acid derivative as a by-production will not occur and a complicated separating process is not required. Since a dangerous reagent is not used, procedures are simple and reaction processed are a few and a time required for the synthesis can be shortened.</abstract><edition>6</edition><oa>free_for_read</oa></addata></record> |
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| subjects | CHEMISTRY HETEROCYCLIC COMPOUNDS HUMAN NECESSITIES HYGIENE MEDICAL OR VETERINARY SCIENCE METALLURGY ORGANIC CHEMISTRY PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS |
| title | PRODUCTION OF 1-POSITION SUBSTITUTED PYRROLE-3-CARBOXYLIC ACID DERIVATIVE |
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