Bajwa et al., 1969 - Google Patents

Reaction of propionaldehyde with N′-methyl-2, 6-dimethylphenylhydrazine hydrochloride. The dienone–imine intermediate in the Fischer indole synthesis and its …

Bajwa et al., 1969

View PDF
Document ID
15071445710311837775
Author
Bajwa G
Brown R
Publication year
Publication venue
Canadian Journal of Chemistry

External Links

Snippet

When N′-methyl-2, 6-dimethylphenylhydrazine hydrochloride was condensed with propionaldehyde by azeotropic removal of water in refluxing benzene for 10–12 min, a solid mixture was obtained which contained no aromatic ring system but instead possessed …
Continue reading at cdnsciencepub.com (PDF) (other versions)

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic 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
    • C07D207/18Heterocyclic 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
    • C07D207/22Heterocyclic 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 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
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D251/00Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2103/00Systems containing at least three condensed rings
    • C07C2103/02Ortho- or ortho- and peri-condensed systems
    • C07C2103/04Ortho- or ortho- and peri-condensed systems containing three rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by C07D451/00 - C07D477/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton

Similar Documents

Publication Publication Date Title
Benson et al. Chemical reactions of caprolactam
Carboni et al. Aromatic azapentalenes. I. dibenzo-1, 3a, 4, 6a-tetraazapentalene and dibenzo-1, 3a, 6, 6a-tetraazapentalene. New heteroaromatic systems
DE69010851T2 (en) Isoindolone derivatives, their preparation and their use as intermediates for the preparation of substance P antagonists.
Dobson et al. The synthesis of 7-alkoxyindoles
Bornstein et al. The synthesis of α-amino-o-tolualdehyde diethylacetal and its attempted conversion to pseudoisoindole
Tormos et al. The indophenine reaction revisited. Properties of a soluble dialkyl derivative
Carlin et al. Studies on the Fischer Indole Synthesis. I
Bajwa et al. Reaction of propionaldehyde with N′-methyl-2, 6-dimethylphenylhydrazine hydrochloride. The dienone–imine intermediate in the Fischer indole synthesis and its conversion to the indole structure
Leonard et al. The Synthesis of Pyrrolizidines. VI. Stereochemical Correlation of 1-Methyl-and 1-Hydroxymethylpyrrolizidine Isomers with Certain Alkaloid Products1
US4282355A (en) Process for the manufacture of bis-benzoxazolyl-stilbene compounds
Ajao et al. The preparation and oxidative dimerisation of 2‐acetyl‐7‐hydroxy‐1, 2, 3, 4‐tetrahydroisoquinoline. A new approach to tetrahydroisoquinoline synthesis
Evans et al. Molecular rearrangements. VIII. The equilibration of 3, 3-dimethyl-2-phenyl-and 2, 3-dimethyl-3-phenyl-3H-indoles1
Reckhow et al. Hexahydroindolo [2, 3-a] quinolizine1
US2766304A (en) Process for preparing azulenes
US2470108A (en) Heterocyclic amines
US3042684A (en) J-ethtl-jj-nitrovinylindole
Bajwa et al. Fischer indole synthesis. The reaction of N′-alkyl-2, 6-dialkylphenylhydrazines with cyclohexanone
Lewis et al. Rearrangements in the furan series. I. The reaction between furfuraldehyde and aniline
Bajwa et al. The dienone–imine intermediate in the Fischer indole synthesis
US4506078A (en) 7-Nitroindoles
Cava et al. Condensed Cyclobutane Aromatic Compounds. XXIV. The Mechanism of Thermal Rearrangement of the Linear Benzocyclobutadiene Dimer: Synthesis of 9, 10-Benzocyclobutenoanthracene1
Southwick et al. 1-Carbamoyl-and 1-aminomethyl-1, 4-dihydropyrrolo [3, 4-b] indole derivatives. Indole formation by fragmentation of strain-barrier stabilized 2-aminoindoline derivatives
Bajwa et al. Fischer indole synthesis. The reaction of N′-methyl-2, 6-dimethylphenylhydrazine hydrochloride with 2-methylcyclohexanone and 2, 6-dimethylcyclohexanone
Suzuki Structure Proof of Diarylmethanes Formed in the Jacobsen Reaction of Monochlorotetramethylbenzenes
Brian et al. New Derivatives of 9-Amino-1, 2, 3, 4-tetrahydroacridine