Synthetic Communications

doi: 10.1080/00397910701575566pmid: N/A

Graphical Abstract Section

Banik, Bimal K.; Mukhopadhyay, Chhanda; Logan, Curtis R.; Becker, Frederick F.

doi: 10.1080/00397910701572209pmid: N/A

Abstract A simple optical resolution of dibenzo[a,g]fluorenol has been accomplished via borontrifluoride‐mediated Ferrier rearrangement reaction.

Chavan, Subhash P.; Khobragade, Dushant A.; Thakkar, Mahesh; Kalkote, Uttam R.

doi: 10.1080/00397910701572266pmid: N/A

Abstract A practical total synthesis of antidepressant (±)‐venlafaxine is disclosed.

Romanelli, Gustavo P.; Sathicq, Angel G.; Autino, Juan C.; Baronetti, Graciela; Thomas, Horacio J.

doi: 10.1080/00397910701572332pmid: N/A

Abstract The Biginelli reaction is performed in an efficient, simple, solvent‐free procedure, using a small amount of H6P2W18O62 · 24H2O, a reusable heteropolyacid catalyst with Wells–Dawson structure. Both aromatic and aliphatic aldehydes, and different β‐dicarbonyl compounds and urea or thiourea, were used as starting materials. Seventeen examples of dihydropyrimidinones and dihydropyrimidinethiones were prepared by heating the reactants either in refluxing acetonitrile or in the absence of solvent. Operational simplicity, the use of a noncorrosive, reusable catalyst in solventless conditions, short reaction times, and very good to excellent yields in most of the selected examples are the main advantages of the method.

Banerjee, Ajoy K.; Pineda, Johan J.; Mora, Henry D.; Laya, Manuel S.

doi: 10.1080/00397910701572431pmid: N/A

Abstract The ketoesters 3 and 4, obtained by the condensation of 2‐cyclohexanone carboxylate and 1‐chloro‐3‐pentanone, were heated with 2,3‐dichloro‐5,6‐dicyanobenzoquinone (DDQ) to yield the dienones 5 and 6, which on hydrolysis with potassium t‐butoxide and dimethyl sulfoxide afforded tetralin 8. These were converted to tetralone 10 by methylation and oxidation respectively. Further methylation of 10 yielded tetralone 11.

Rojas, Giovanni; Baughman, Travis W.; Wagener, Kenneth B.

doi: 10.1080/00397910701572456pmid: N/A

Abstract A synthetic pathway that produces alkyl α,ω‐cyanodiolefins in quantitative yield is described, applying chemistry that is based on simple α‐alkylation of alkyl nitriles. Three amide bases, lithium 2,2,6,6‐tetramethylpiperidide, lithium diisopropylamide, and sodium amide, are used to create the α‐carbanions that undergo substitution with various alkylating agents. Optimization leads to essentially quantitative conversions for every substrate/example reported herein, which will prove useful in many synthetic schemes.

Liu, Fei; You, Qi‐Dong

doi: 10.1080/00397910701572555pmid: N/A

Abstract An efficient and environmentally friendly synthesis of tetrahydro‐β‐carboline hydrochlorides via Pictet–Spengler reaction was described. Tryptamine hydrochlorides were used as the reactant and no additional acid catalyst was needed. This reaction was completed within 2.5–9 min in good yield.

Jameleddine, Khiari; Thouraya, Gmiza; Adnen, Hadj Ayed Med; Hassine Béchir, Ben

doi: 10.1080/00397910701572571pmid: N/A

Abstract A highly efficient and versatile method for the synthesis of 3‐acyl‐5‐aryl or arylsulfonylpyridin‐2‐ones and 3‐alkyl‐5‐aryl‐2‐hydroxybenzamides in one step via regiospecific cyclocondensation reaction of β‐keto‐amides with vinamidinium salts is described.

Abdou, Wafaa M.; Kamel, Azza A.

doi: 10.1080/00397910701572670pmid: N/A

Abstract Treatment of 2H‐3,1‐benzoxazine‐2,4(1H)‐dione (1a) with vinyltriphenylphosphonium bromide (2a) gives substituted benzoazepine 8a (48% yield) and indolizinone 12 (27% yield), whereas substituted quinolinone 15 and benzoazepine 8b were isolated from the reaction of N‐methylisatoic anhydride (1b) and 2a. Furthermore, a series of quinoline derivatives was synthesized from the reactions of 1a and 1b with allyl‐(2b), alkyl‐(2c), (2d), and cyanomethyl‐(3) triphenylphosphonium salts.

Abd El‐Rahman, Naglaa M.; El‐Kateb, Ahmed A.; Mady, Mohamed F.

doi: 10.1080/00397910701572696pmid: N/A

Abstract Use of microwave irradiation in the synthesis of arylidenemalononitrile and benzopyran derivatives in water without catalyst is a clean method with high yield.