2128-90-7

Upstream product

• 4055-00-9 6-phenyl-3,4-dihydropyran-2-one 
• 116153-74-3 2-oxo-6-phenyl-2H-pyran-4-carboxylic acid 
• 66838-71-9 1,1-Dichlor-5-phenyl-pentadien-(1,3)-on-⁽⁵⁾ 
• 56427-26-0 1,1-dichloro-5-phenyl-pent-1-en-4-yn-3-ol 
• 16900-64-4 4-phenylbut-1-en-3-yne-1,1-dicarboxylic acid 
• 2128-99-6 5-oxo-5-phenyl-pent-2ξ-enoic acid 
• 107418-81-5 2-oxo-6-phenyl-2H-pyran-3,5-dicarboxylic acid diethyl ester 
• 4660-17-7 rac-6-phenyl-5,6-dihydro-2H-pyran-2-one 
• 115411-36-4 6-phenyl-4-methylsulfanyl-2-oxo-2H-pyran 
• 27948-29-4 (Z)-5-phenyl-2-penten-4-ynoic acid 
• 60-29-7 diethyl ether 
• 7726-95-6 bromine 
• 29898-32-6 2,4-dichloro-1-iodo-benzene 
• 344340-95-0 5-iodo-6-phenyl-2(2H)-pyranone 

Downstream Products

• 67793-58-2 3-anilino-5-oxo-5-phenyl-valeric acid anilide 
• 97583-69-2 C₃₀H₂₂N₂O₄ 
• 81536-51-8 2,3-Diphenyl-phosphinine 
• 91597-38-5 methoxy-5 dimethyl-2,5 phenyl-1 hexene-2 one-1 
• 91611-55-1 trimethyl-2,3,4 phenyl-1 hexanedione-1,5 
• 91597-44-3 methoxy-5 dimethyl-2,5 phenyl-1 hexene-3 one-1 
• 5186-21-0 3-iodo-6-phenyl-2-pyrone 
• 98-86-2 acetophenone 
• 65-85-0 benzoic acid 
• 92-92-2 biphenyl-4-carboxylic acid 
• 6263-84-9 1,3,5-triphenyl-1,5-pentanedione 
• 29179-23-5 5-methyl-1-phenylhexan-2,4-dien-1-one 
• 25552-15-2 3-Methyl-1-phenyl-hexandion-(1,5) 
• 25552-16-3 5-Hydroxy-5-methyl-1-phenyl-hex-3-en-1-on 

Relevant academic research and scientific papers

A novel route to 6-substituted and 5,6-disubstituted 2-pyrones

6-Alkyl- and 6-(1-alkenyl)-5-iodo-2-pyrones, which are available as major products by reaction of the corresponding (Z)-2-en-4-ynoic acids with iodine and NaHCO3 in CH3CN, undergo insertion of activated zinc metal into their carbon-iodine bond to provide the corresponding 5-(iodozinc)-2-pyrones. Hydrolysis of these organometallics gives 6-substituted 2-pyrones in satisfactory yields including two natural products. On the other hand, the Pd-catalyzed reaction of the organozincs either with an activated alkenyl halide or with activated and deactivated (hetero)aryl halides provides 5,6-disubstituted 2-pyrones in fair to good yields.

Catalytic and selective conversion of (Z)-2-en-4-ynoic acids to either 2H-pyran-2-ones in the presence of ZnBr2 or (Z)-5-alkylidenefuran-2(5H)-ones in the presence of Ag2CO3

Treatment of (Z)-5-alkyl-2-en-4-ynoic acids (1), prepared by the Pd-catalyzed alkynylzinc-β-haloacrylic acid coupling, with 5-10 mol% of ZnBr2 can produce 6-alkyl-2H-pyran-2-ones (2) along with minor amounts of (Z)-5-alkylidenefuran-2(5H)-ones (3) in >90% combined yields, with often very high (≈95/5) pyranone/furanone ratios. On the other hand, lactonization of 1 catalyzed by Ag2CO3 provides a selective synthesis of (Z)-5-alkylidenefuran-2(5H)-ones (3) in >90% yields along with minor amounts (≤5%) of 2.

Palladium-catalyzed synthesis of stereodefined 3-[(1,1-unsymmetrically disubstituted)methylidene]isobenzofuran-1(3H)-ones and stereodefined 5-[(1,1- unsymmetrically disubstituted)methylidene]furan-2(5H)-ones

Treatment of (hetero)aryl halides with 2-(1-alkynyl)benzoic acids or (Z)-2-en-4-ynoic acids in the presence of K2CO3 and a catalytic amount of Pd(PPh3)4 provides reaction mixtures in which stereodefined 3-[(1,1-

Regioselective Synthesis of 5-Metalated 2-Pyrones by Intramolecular Oxymetalation of Carbonyl-ene-yne Compounds Using Indium Trihalide

The oxyindation of carbonyl-ene-yne compounds with indium trihalides proceeded efficiently to give di-, tri-, and tetrasubstituted 2-pyrones bearing a carbon-indium bond. The metalated 2-pyrone and a zwitterion intermediate were identified by X-ray crystallographic analysis. The application of organoindium compounds to oxidation or cross-coupling provided easy access to various multifunctionalized 2-pyrones. Some 2-pyrone derivatives show intense fluorescence only in the solid state (aggregation-induced emission).

Rhodium-catalyzed decarboxylative and dehydrogenative coupling of maleic acids with alkynes and alkenes

The dehydrogenative coupling of maleic acids with alkynes proceeds smoothly accompanied by decarboxylation under rhodium catalysis to produce variously substituted α-pyrone derivatives. The catalyst system is also applicable to the coupling with 1,3-diyne

Gold(I)-catalyzed cycloisomerization of β-alkynylpropiolactones to substituted α-pyrones

Substituted α-pyrones were straightforwardly synthesized in good to excellent yields by a new gold(I)-catalyzed rearrangement of β-alkynylpropiolactones.

Regiocontrolled intramolecular cyclizations of carboxylic acids to carbon-carbon triple bonds promoted by acid or base catalyst

We systematically investigated, for the first time, the relationship between regioselectivity and acid/base effects in the cyclization reactions between carboxylic acids and carbon-carbon triple bonds. We found novel acid- and base-promoted cyclizations to selectively give isocoumarin or pyran-2(2H)-one and phthalide or furan-2(5H)-one skeletons, respectively, and established a catalytic version of regioselective heterocyclic ring synthesis. Density functional theory calculations and application to a short route to thunberginol A were also described.

Phosphine-catalyzed synthesis of 6-substituted 2-pyrones: Manifestation of E/Z-isomerism in the zwitterionic intermediate

(Chemical Equation Presented) We report a one-step phosphine-catalyzed annulation between aldehydes and ethyl allenoate to form 6-substituted 2-pyrones. The mechanistic rationale for this reaction requires explicit discussion of the E/Z-isomerism of the zwitterionic intermediate formed by the addition of a phosphine to the allenoate. Sterically demanding trialkylphosphines facilitate the shift of equilibrium toward the E-isomeric zwitterion and lead to the formation of 6-substituted 2-pyrones. Various aromatic as well as aliphatic aldehydes undergo the transformation in moderate to excellent yield.

One-step synthesis of alpha-pyrones from acyl chlorides by the Stille reaction.

Palladium-catalyzed stereoselective annulation of a functional vinylstannane by acyl chlorides gives the corresponding alpha-pyran-2-ones in good yields. This annulation most probably proceeds through a Stille reaction/cyclization sequence.

SILVER CATALYZED CYCLIZATION OF ALKYNOIC ACIDS: EFFICIENT SYNTHESIS OF 3-ALKYLIDENEPHTHALIDES, γ-ALKYLIDENEBUTENOLIDES AND γ-ALKYLIDENEBUTYROLACTONES

The cyclization of 2-pentynylbenzoic acid (1a) catalyzed by various silver salts and solvents was investigated. 2-Alkynylbenzoic acids (1), 2-alken-4-ynoic acids (7), and 4-alkynoic acids (4) were effectively cyclized to the corresponding phthalides (2), γ-alkylidenebutenolides (8), and γ-alkylidenebutyrolactones (5) with silver iodide or silver as catalyst in DMF regio- and stereo-selectively in excellent yield, respectively.