[go: up one dir, main page]

Chiu et al., 1987 - Google Patents

Novel synthesis of 3 H-pyrroles, and novel intermediates in the Paal–Knorr 1 H-pyrrole synthesis: 2-hydroxy-3, 4-dihydro-2 H-pyrroles from 1, 4-diketones and liquid …

Chiu et al., 1987

View PDF
Document ID
263439864965385451
Author
Chiu P
Lui K
Maini P
Sammes M
Publication year
Publication venue
Journal of the Chemical Society, Chemical Communications

External Links

Snippet

Reaction of 2, 2-dimethyl-1, 4-diketones with liquid ammonia gives high yields of isolable 2- hydroxy-3, 4-dihydro-2H-pyrroles (3) and (5) which are readily dehydrated to give separable mixtures of 3H-pyrroles and methylenedihydropyrroles, while less-substituted 1, 4-diketones …
Continue reading at citeseerx.ist.psu.edu (PDF) (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C07D307/48—Furfural
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic 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
    • C07D307/93—Heterocyclic 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 condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • C07D207/22—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 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulfur 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Similar Documents

Publication Publication Date Title
Cava et al. Synthetic route to benzo [c] thiophene and the naphtho [c] thiophenes
Enders et al. Organocatalytic one-pot asymmetric synthesis of functionalized tricyclic carbon frameworks from a triple-cascade/Diels-Alder sequence
Chiu et al. Novel synthesis of 3 H-pyrroles, and novel intermediates in the Paal–Knorr 1 H-pyrrole synthesis: 2-hydroxy-3, 4-dihydro-2 H-pyrroles from 1, 4-diketones and liquid ammonia
Boukouvalas et al. Facile access to 4-aryl-2 (5H)-furanones by Suzuki cross coupling: efficient synthesis of rubrolides C and E
Maes et al. A new approach towards the synthesis of 3-amino-6-(hetero) arylpyridazines based on palladium catalyzed cross-coupling reactions
Ochiai et al. Oxidative decarboxylation of cyclic amino acids and dehydrogenation of cyclic secondary amines with iodosobenzene
Antonioletti et al. A convenient approach to furan derivatives by I2-induced cyclisation of 2-alkenyl substituted 1, 3-dicarbonyl compounds
Radhakrishna et al. Iodobenzene dichloride-an efficient reagent for preparation of nitrile oxides from aldoximes
Somei et al. PYRROLO23-b] INDOLES1
Godard et al. Convergent synthesis of streptonigrin and Lavendamycin analogues
Schinzer et al. Intramolecular cyclizations of allyl-and propargylsilanes
Page et al. Asymmetric oxidation of dithiane derivatives: enantiomerically pure 1, 3-dithiane 1-oxide
Engler et al. Switchable regioselectivity in lewis acid-promoted reactions of 1, 4-benzoquinone monoimides with styrenyl systems: Selective syntheses of either 2-aryl-2, 3-dihydrobenzofurans or 2-aryl-2, 3-dihydroindoles
Alcaide et al. PdII‐Catalyzed Domino Heterocyclization/Cross‐Coupling of α‐Allenols and α‐Allenic Esters: Efficient Preparation of Functionalized Buta‐1, 3‐dienyl Dihydrofurans
Srikrlshna et al. A radical cyclisation route to (±)-Andirolactone, a spiro-γ-butyrolactone
Marco-Contelles et al. Synthesis of chiral, densely functionalized medium-sized rings from carbohydrate precursors via regioselective exo/endo-primary alkyl radical cyclizations
Allin et al. Stereoselective synthesis of isoquinoline derivatives from bicyclic lactam templates
Miyake et al. Novel electron-transfer oxidation of Lipshutz cuprates with 1, 4-benzoquinones: an efficient homo-coupling reaction of aryl halides and its application to the construction of macrocyclic systems
Kim et al. A facile synthesis of 3-aryl-substituted-benzothiophenes via a lewis acid mediated cyclization of 2-arylthio-acetophenones
Ruano et al. Anchimeric assistance of the sulfinyl group in the hydrolysis of cyano groups: a new mild method for the reduction of sulfoxides
Benedetti et al. Cyclization of γ, δ-epoxy-α-cyanosulphones. A simple, diastereoselective route to cyclopropane carboxylic acids.
Rassu et al. General approach to hydroxylated α-amino acids exploiting N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy) pyrrole
Sasaki et al. Synthesis of adamantane derivatives. 34. Synthesis of 2, 4-methanoadamantane and 2, 4-methanoprotoadamantane
Vankar et al. A Simple Synthesis of 3-Nitrocycloalkenones and Their Acetals
Hirao et al. Tetracarbonyl nickel induced reaction of gem-dibromocyclopropanes with alcohols or amines.: Versatile synthesis of cyclopropanecarboxylic acid derivatives