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synthesis
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Flashcards in this deck (48)

๊ฒ€์ƒ‰ ์ค‘...

  • Which intramolecular substitution products are listed for synthesizing three-membered rings?

    • Oxiran (epoxide)
    • Aziridin
    synthesis 3-ring

  • Which named procedure converts a precursor into an epoxide (oxiran) in the notes?

    • Wartz -> Oxiran / Epoxide
    epoxide wartz

  • Which named procedure converts a precursor into an aziridine in the notes?

    • Wenker -> Aziridin
    aziridine wenker

  • Which reagents are specified for Mitsunobu-cyclisation to form three-membered rings?

    • PPh3 and DEAD
    mitsunobu reagents

  • What two general transformations are listed for making three-membered heterocycles?

    • Epoxidation
    • Aziridination
    3-ring transformations

  • How can three-membered rings be synthesized from carbonyls or imines according to the notes?

    • Using Sulfur-ylid
    sulfur-ylid 3-ring

  • Name two approaches listed for synthesizing four-membered rings.

    • Intramolecular substitution with haloalcohols/haloamines
    • [2+2] cycloaddition
    4-ring methods

  • Which photochemical reaction is listed for making four-membered rings from an alkene and a carbonyl?

    • Paterno-Bรผchi-Reaktion (Alken + Carbonyl)
    paterno-bรผchi photochemistry

  • Which reaction combining a keten and an imine is listed for four-membered ring synthesis?

    • Staudinger-Synthese (Keten + Imine)
    staudinger 4-ring

  • List the general routes given for synthesizing five-membered rings.

    • Cyclisation
    • (3+2) Cycloaddition
    5-ring cycloaddition

  • Which 1,3-dipoles or related species are listed for (3+2) cycloadditions to form five-membered rings?

    • Azide
    • Nitriloxide
    • Nitrone
    • Azomethin-ylide
    dipole 5-ring

  • Which two general methods are listed for synthesizing six-membered rings?

    • Cyclisation
    • Hetero-Diels-Alder
    6-ring methods

  • What reagents form pyrrole in the Paalโ€“Knorr synthesis?

    • Ammoniak/primary amines and 1,4-dicarbonyl
    paal-knorr pyrrole heterocycle

  • What reagent combination gives furan in the Paalโ€“Knorr synthesis?

    • 1,4-dicarbonyl
    paal-knorr furan heterocycle

  • What is required to synthesize thiophene via Paalโ€“Knorr?

    • 1,4-dicarbonyl and a Sulfur source (P2S5 or Lawesson-Reagent)
    paal-knorr thiophene heterocycle

  • Which starting materials are used in the Knorr synthesis to make pyrrole?

    • alpha-Aminoketone and beta-dicarbonyl
    knorr pyrrole heterocycle

  • Which reagents are paired in the Van Leusen method to form pyrrole?

    • Imines and TosMIC
    van-leusen pyrrole heterocycle

  • What are the key reagents for the Fischer synthesis of a heterocycle with one heteroatom and two rings (one 5-ring)?

    • Arylhydrazin and Aldehyde/ketone
    fischer heterocycle synthesis

  • What starting materials and catalyst are used in the Castro synthesis for a fused heterocycle?

    • o-Halogenaniline, Alkine, Cu-Catalyst
    castro heterocycle copper

  • What single substrate is listed for the Reissert synthesis in this overview?

    • o-Nitrotoluol
    reissert heterocycle

  • Which reagents and catalyst are used in the Moriโ€“Banโ€“Heck synthesis?

    • o-Halogenaniline, Alkene, Pd-Catalyst
    mori-ban-heck heterocycle palladium

  • What three components form 1,3-azoles in the Debusโ€“Radiszewski synthesis?

    • 1,2-dicarbonyl, aldehyde, 2 Ammoniak/primary amines
    debus-radiszewski 1,3-azoles heterocycle

  • What reagents are required for the Hantzsch-type thiazole synthesis from halogencarbonyls?

    • alpha-halogencarbonyl and Thioamide
    hantzsch thiazole halogencarbonyl

  • In Van Leusen routes to oxazoles and imidazoles, which partners are used with TosMIC?

    • Aldehyde (Oxazoles) / Amine (Imidazole) with Base (K2CO3/NaOMe)
    van-leusen tosmic azoles

  • What substrates form pyrazole according to the overview for 1,2-azoles?

    • 1,3-dicarbonyl and hydrazine
    pyrazole 1,2-azoles hydrazine

  • Which reagents are listed to synthesize 'Isoxazol'?

    • 1,3-dicarbonyl
    • hydroxylamine
    isoxazol reagents

  • Which dipolar cycloaddition pair is given to form 'Isoxazol'?

    • Nitriloxid + Alkine
    isoxazol cycloaddition

  • Which dipolar cycloaddition pair is given to form 'Pyrazol'?

    • Diazomethan + Alkine
    pyrazol cycloaddition

  • Which reagents are used in the Huisgen-Alky-Azid cycloaddition to make 1,2,3-triazole?

    • Azid + Alkine
    triazole huisgen

  • What are the components of the Hantzsch synthesis listed for a one-heteroatom six-membered ring?

    • 2 beta-dicarbonyl
    • aldehyde
    • NH3/Ammoniumacetate
    hantzsch synthesis

  • Which three-component assembly is listed as coming from 1,5-dicarbonyl and NH3?

    • From 1,5-dicarbonyl and NH3
    hantzsch alternative

  • Which [2+2+2] cycloaddition partners are listed to build a one-heteroatom six-membered ring?

    • 2 Alkines + 1 Nitrile
    cycloaddition 2+2+2

  • Which [4+2] cycloaddition partners are listed for making a one-heteroatom six-membered ring?

    • Dielsโ€“Alder (general [4+2] cycloaddition)
    diels-alder 4+2

  • Which starting heterocycles are listed as precursors to one-heteroatom six-membered rings with alkine/alkene?

    • Oxazoles + Alkine/Alkene
    oxazole ring-formation

  • Which starting heterocycle is listed to form six-membered rings with electron-rich alkines?

    • Triazines + electron rich alkines
    triazine synthesis

  • What are the reagents for the Combes synthesis to form one-heteroatom, two fused six-rings?

    • aniline + 1,3-dicarbonyl
    combes synthesis

  • What starting materials does the Friedlรคnder synthesis use for fused six-membered ring systems?

    • o-Aminobenzaldehyd + Carbonyl
    friedlander synthesis

  • What is the starting material listed for the Pictet-Gams synthesis?

    • beta-hydroxy-beta-phenylethylamide
    pictet-gams synthesis

  • Which reagents are given to synthesize 'Pyridazin'?

    • 1,4-dicarbonyls + hydrazine
    pyridazin reagents

  • Which cycloaddition is listed as an alternative route to 'Pyridazin'?

    • [4+2] Cycloaddition of tetrazines with alkines
    pyridazin cycloaddition

  • Which reagents are listed to form 'Pyrimidin'?

    • 1,3-dicarbonyls + Amidin/Urea
    pyrimidin reagents

  • Which reagents are listed to form 'Pyrazin'?

    • 1,2-dicarbonyls + 1,2-diamines
    pyrazin reagents

  • What starting material is mentioned for the syntheses?

    2-aminoketones

    precursor

  • Which target molecule class is specified under 'Synthesis'?

    Purine

    purine

  • Which two topics are noted as 'just need to know what its about'?

    • Eintopfreaktion
    • prรคbiotische synthesen
    topics

  • Name three of the important reactions listed.

    • Vilsmeier Haack
    • Pictet-Spengler Reaction
    • Dipolar cycloaddition
    reactions

  • List all important reactions mentioned.

    • Vilsmeier Haack
    • Pictet-Spengler Reaction
    • Dipolar cycloaddition
    • Suzuki miyaura
    • Benzoinkondensation
    • Ziegler-reaktion
    • Chichibabin-reaction
    reactions named

  • Is 'Dipolar cycloaddition' included among the important reactions?

    Yes

    reactions
ํ•™์Šต ๋…ธํŠธ

Overview

Concise guide to common synthetic methods for making 3โ€“6 membered carbocycles and heterocycles, plus selected named reactions used to assemble heteroatom-containing rings.

General strategies for small-ring formation (3โ€“4 members)

  • 3-membered rings (epoxides, aziridines)
  • Intramolecular substitution: haloalcohols/haloamines cyclize to epoxides/aziridines.
  • Wartz โ†’ Oxiran / Epoxide: listed as a route to epoxides (see course notes).
  • Wenker โ†’ Aziridin: specific transformation to aziridines.
  • Mitsunobu cyclisation: intramolecular Mitsunobu (PPh3 + DEAD) can form strained rings from alcohols and nucleophiles.
  • Direct addition: epoxidation of alkenes; aziridination of alkenes with nitrenoid sources.

  • Sulfur ylides: convert carbonyls/imines into epoxides/aziridines via ylides.

  • 4-membered rings (cyclobutanes, azetidines, oxetanes)

  • Intramolecular substitution of suitably spaced haloalcohols/haloamines.
  • [2+2] Cycloaddition: photochemical or thermal [2+2] between alkenes or ketenes and alkenes.
  • Paternoโ€“Bรผchi: carbonyl + alkene โ†’ oxetane (photochemical [2+2]).
  • Staudinger-type: ketene + imine โ†’ ฮฒ-lactam (a formal [2+2] addition).

Strategies for 5-membered rings (general)

  • Main pathways:
  • Intramolecular cyclisation of linear precursors.
  • (3+2) Cycloadditions (dipolar cycloadditions) to build 5-membered frameworks.

  • Formation from functional group interconversion (azides, nitrones, nitrile oxides, azomethine ylides).

  • Typical dipoles and partners:

  • Azides โ†’ 1,2,3-triazoles (via cycloaddition with alkynes).
  • Nitrile oxides โ†’ isoxazoles (with alkynes).
  • Nitrones โ†’ isoxazolidines / related 5-membered products.
  • Azomethine ylides โ†’ pyrrolidine frameworks via 1,3-dipolar cycloaddition.

Strategies for 6-membered rings (general)

  • Cyclisation of appropriate 1,5- or 1,6- precursors.
  • Hetero-Dielsโ€“Alder (4+2): builds oxygen- or nitrogen-containing six-membered rings.
  • [2+2+2] cycloadditions (for N-containing aromatics from alkynes + nitriles) often used for heteroaromatics.

One heteroatom in a 5-membered ring (specific named syntheses)

  • Paalโ€“Knorr synthesis
  • Pyrroles: primary amine or ammonia + 1,4-dicarbonyl.
  • Furans: acid-catalyzed cyclization of 1,4-dicarbonyls.
  • Thiophenes: 1,4-dicarbonyl + sulfur source (P2S5 or Lawesson reagent).

  • Alternative: build 1,4-dicarbonyls from alkynes via Michael addition or Stetter reaction (NHC-catalyzed).

  • Knorr synthesis

  • Pyrroles from an ฮฑ-amino ketone plus a ฮฒ-dicarbonyl compound.

  • Van Leusen

  • Pyrrole formation using TosMIC and imines (or related partners).

One heteroatom, fused/bi-cyclic 5-ring systems (routes)

  • Fischer synthesis: arylhydrazine + carbonyl โ†’ indole-type chemistry (for fused 5-rings).
  • Castro, Reissert, Moriโ€“Banโ€“Heck: cross-coupling or annulation strategies starting from o-halogen anilines, alkynes, alkenes or nitroarenes to build fused N-heterocycles.

1,3-Azoles (oxazoles, thiazoles, imidazoles)

  • Debusโ€“Radiszewski: 1,2-dicarbonyl + aldehyde + ammonia/primary amine โ†’ imidazole core.
  • Hantzsch-type (thiazole): ฮฑ-halo carbonyl + thioamide โ†’ thiazole.
  • Van Leusen (TosMIC): aldehyde + TosMIC โ†’ oxazole (or with amine โ†’ imidazole) using base (K2CO3 or NaOMe).

1,2-Azoles and related (pyrazoles, isoxazoles)

  • From 1,3-dicarbonyls: condensation with hydrazine โ†’ pyrazoles.
  • Isoxazoles: 1,3-dicarbonyl + hydroxylamine forms isoxazoles.
  • Dipolar cycloadditions:
  • Nitrile oxides + alkynes โ†’ isoxazoles.
  • Diazomethane + alkynes โ†’ pyrazoles (via 1,3-dipolar addition).

1,2,3-Triazoles

  • Huisgen 1,3-dipolar cycloaddition: azide + alkyne โ†’ 1,2,3-triazole (thermal or Cu(I)-catalyzed click variant).

One heteroatom in a 6-membered ring (methods)

  • Hantzsch synthesis: two ฮฒ-dicarbonyls + aldehyde + NH3 / ammonium acetate โ†’ dihydropyridine โ†’ pyridine derivatives after oxidation.
  • From 1,5-dicarbonyl + NH3: direct cyclisation to 6-membered N-heterocycles.
  • [2+2+2] cycloadditions: two alkynes + nitrile โ†’ substituted pyridines.
  • Dielsโ€“Alder (4+2): hetero-Dielsโ€“Alder builds oxygen- or nitrogen-containing six-membered rings.
  • From azoles/triazines: ring transformation or cycloaddition of electron-rich alkynes/alkenes to give 6-membered heterocycles.

One heteroatom, two fused 6-rings (bicyclic N-heterocycles)

  • Combes synthesis: aniline + 1,3-dicarbonyl โ†’ quinoline derivatives.
  • Friedlรคnder synthesis: o-aminobenzaldehyde + ketone โ†’ quinoline cores.
  • Pictetโ€“Gams: cyclization of ฮฒ-hydroxy-ฮฒ-phenylethylamide to form tetrahydroisoquinoline frameworks.

Two heteroatoms in one ring (diazines and related)

  • Pyridazine (1,2- or 1,6- diazine)
  • From 1,4-dicarbonyls + hydrazine.

  • Also accessible by [4+2] cycloaddition of tetrazines with alkynes (retro-[4+2] extrusion of N2).

  • Pyrimidine

  • From 1,3-dicarbonyls condensed with amidines or urea-type N-sources.

  • Pyrazine

  • From 1,2-dicarbonyls + 1,2-diamines or from 2-aminoketones.

Purines and polycycles

  • Purine syntheses often involve multi-step ("Eintopf") or prebiotic-type one-pot assemblies; course note: know concept and general assembly logic rather than every variant.

Other named reactions and useful tools (select list)

  • Vilsmeierโ€“Haack formylation
  • Pictetโ€“Spengler cyclization (ฮฒ-arylethylamines with aldehydes)
  • Dipolar cycloaddition methods for 5-membered rings
  • Suzukiโ€“Miyaura cross-coupling for assembling substituted rings
  • Benzoin condensation for building ฮฑ-hydroxy ketones
  • Ziegler-type reactions (polyolefin or metal-mediated transformations)
  • Chichibabin reaction (nucleophilic aromatic substitution on pyridines)

Practical tips for studying ring syntheses

  • Group methods by ring size and by the number/type of heteroatoms to simplify memorization.
  • Learn one representative mechanism per named reaction (key intermediates and driving force).
  • Recognize common building blocks: 1,3- and 1,4-dicarbonyls, alkynes, azides, nitrile oxides, hydrazines, TosMIC.
  • Remember common catalysts/reagents associated with names (e.g., PPh3/DEAD for Mitsunobu, TosMIC + base for Van Leusen, NH3/acetate for Hantzsch).

Quick reference: common ring-building motifs

  • 3-membered: intramolecular substitution, epoxidation/aziridination, sulfur ylides.
  • 4-membered: [2+2] cycloaddition, Paternoโ€“Bรผchi, ketene + imine (ฮฒ-lactams).
  • 5-membered (hetero): Paalโ€“Knorr, Knorr, Van Leusen, (3+2) dipolar cycloadditions.
  • 6-membered (hetero): Hantzsch, Dielsโ€“Alder, [2+2+2] cycloadditions, ring transformations.