GB1099500A - Preparation of pyrrole derivatives - Google Patents

Preparation of pyrrole derivatives

Info

Publication number
GB1099500A
GB1099500A GB5178064A GB5178064A GB1099500A GB 1099500 A GB1099500 A GB 1099500A GB 5178064 A GB5178064 A GB 5178064A GB 5178064 A GB5178064 A GB 5178064A GB 1099500 A GB1099500 A GB 1099500A
Authority
GB
United Kingdom
Prior art keywords
dimethyl
dicarboxylate
hydrogen
carbon
azlactone
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
GB5178064A
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB1099500A publication Critical patent/GB1099500A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)

Abstract

Pyrroles of the general formula <FORM:1099500/C2/1> are obtained by contacting an acetylenic compound of the formula R3C=CR4 with an azlactone or mesoionic azlactone of the respective general formulae <FORM:1099500/C2/2> wherein each of R1 to R5 is hydrogen or a monovalent aliphatic, cycloaliphatic or heterocyclic group attached to the ring carbon atom through a carbon to carbon bond or in the case when R5 is other than hydrogen through a carbon to nitrogen bond, with the proviso (a) that when an azlactone of the first formula is used R5 in the resulting pyrrole is hydrogen, and (b) R1 and R5 can together form an alkylene group. The radicals R1 to R5 may be substituted, e.g. by amino, carbalkoxy, CN, halo, isocyanato, nitro, sulpho or thio or other group containing C and H and O, N, or S. The substituent R1 may also be any natural alpha-aminocarboxylic acid residue. The reaction is preferably effected at 0 DEG to 140 DEG C. and preferably in an inert solvent especially benzene, toluene, xylene or dioxane and the process can be conducted in an inert atmosphere, e.g. of nitrogen or argon. The azlactone or mesoionic azlactone may be formed in situ in the reaction system from an appropriate alpha-amino carboxylic acid having primary or secondary amino groups or its N-acyl derivative by cyclization by means of an acid anhydride, e.g. acetic acid, and then reacts immediately after its formation with the acetylenic reactant also present. The acetylenic compound may be acetylene itself or a substituted acetylene, e.g. a propiolic ester, acetylene dicarboxylic ester, dibenzoylacetylene, phenylpropiolic ester, p-chlorophenyl-acetylene, 1 - phenyl - 2 - acetyl - acetylene, 1 - hexyne or propargyl acetate. Several examples are given and the invention also includes as novel products substituted pyrroles of the given general formula in which each of R1 to R5 are hydrogen or a monovalent aliphatic, cycloaliphatic, aromatic or heterocyclic group attached to the ring carbon atom through a carbon to carbon bond or when R5 is other than hydrogen through a carbon to nitrogen bond, with the proviso that (a) at least one of R3 and R4 is an alkoxycarbonyl group, (b) at least one of R1 and R2 is other than hydrogen, and (c) R1 and R5 can together form an alkylene group. The invention also includes per se the following specific products which are products of certain of the examples:-(1) dimethyl 2-phenyl-5-methyl - pyrrole - 3,4 - dicarboxylate, (2) dimethyl 2,5 - diphenylpyrrole - 3,4 - dicarboxylate, (3) dimethyl 2-(0-nitrophenyl)-5-phenylpyrrole - 3,4 - dicarboxylate, (4) dimethyl-2-(p-methoxyphenyl) - 5 - phenylpyrrole - 3,4 - dicarboxylate, (5) methyl 2,5-diphenylpyrrole-3-carboxylate, (6) 2,3,5-triphenyl-4-acetylpyrrole, (7) 2,3,5-tri-phenylpyrrole, (8) dimethyl 2-(a -naphthyl) - 5 - phenylpyrrole - 3,4 - dicarboxylate, (9) dimethyl 2-phenyl-5-p-chlorophenyl-pyrrole 3,4-dicarboxylate, (10) 2,3,4,5 - tetraphenyl - 1 - methylpyrrole, (11) 2,5 - diphenyl - 1 - methyl - 3 - n - butylpyrrole, (12) 1,3 - diphenyl 2,5 - dimethylpyrrole, (13) 1,2 - dimethyl 3,5- (or 4,5-) diphenylpyrrole, and (14) 2,3,5 - triphenyl - 1 - methyl - 4 - benzoyl - pyrrole.
GB5178064A 1963-12-20 1964-12-21 Preparation of pyrrole derivatives Expired GB1099500A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEU0010359 1963-12-20

Publications (1)

Publication Number Publication Date
GB1099500A true GB1099500A (en) 1968-01-17

Family

ID=7567193

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5178064A Expired GB1099500A (en) 1963-12-20 1964-12-21 Preparation of pyrrole derivatives

Country Status (2)

Country Link
DE (1) DE1470387A1 (en)
GB (1) GB1099500A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5776954A (en) * 1996-10-30 1998-07-07 Merck & Co., Inc. Substituted pyridyl pyrroles, compositions containing such compounds and methods of use
US5792778A (en) * 1995-08-10 1998-08-11 Merck & Co., Inc. 2-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5837719A (en) * 1995-08-10 1998-11-17 Merck & Co., Inc. 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU75478A1 (en) 1976-07-28 1978-02-08
EP0182737A3 (en) * 1984-10-16 1986-10-08 Ciba-Geigy Ag 3-phenyl-pyrrole derivatives, process for their preparation and their use as pesticides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5792778A (en) * 1995-08-10 1998-08-11 Merck & Co., Inc. 2-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5837719A (en) * 1995-08-10 1998-11-17 Merck & Co., Inc. 2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5776954A (en) * 1996-10-30 1998-07-07 Merck & Co., Inc. Substituted pyridyl pyrroles, compositions containing such compounds and methods of use

Also Published As

Publication number Publication date
DE1470387A1 (en) 1969-05-29

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