Methoxy facile synthesis

The parent, unsubstituted isochromanone has been caused to react with a variety of aromatic amines to prepare Ar-substituted 1,4-dihydro-3(2.ff)-isoquinolones,4 and with amines to give amides.5 The 6,7-methylenedioxy-3-isochromanone was an intermediate in the synthesis of protopine and its allied alkaloids,6 and for the synthesis of the berberine ring system.7 The 6-methoxy analog was prepared as a potential intermediate in a camptothecin synthesis8 and 8-methoxy-4,5,6,7-tetramethyl-3-isochromanonc was an intermediate in the synthesis of sclerin.9 The compound herein described was the basis of a facile synthesis of ( l )-xylopmins,10 and its reaction with hydrazine has been reported.11... 

Bossio R, Marcaccini S, Pepino R, Torroba T (1999) Studies on isocyanides and related compounds. A facile synthesis of 1-substituted 3-cyano-2-methoxy-3-phenylpyrroles. Heterocycles 50(1) 463 167... 

Dyker, G. Palladium-catalyzed C-H activation of methoxy groups a facile synthesis of substituted 6H-dibenzo[h,d]pyrans. Angew. Chem. 

A facile synthesis of erlotinib, patented by Schnur and Arnold, began with the condensation of readily available ethyl-2-amino-4,5-bis-(2-methoxy-ethoxy)benzoate and formamide to produce the corresponding quinazolinone,... 

A facile synthesis of chiral cyclopalladated compounds, that is, the methoxy-palladation of allylamines, has been reported via the reaction of A,iV-dimethylamino-3-but-l-ene and A,iV-dimethylamino-l-cyclohexene-2-ene with Li2PdCl4 in MeOH. ... 

Oda, K., Sakai, M., and Machida, M., Photochemistry of the nitrogen-thiocarbonyl systems. 30. Intermolecular photoaddition reaction of arenecarbothioamides to 2-methoxy- and 2-(trimethyl-siloxy)furans. Facile synthesis of arene-fused aminobenzoates by novel photoinduced benzannulation, Chem. Pharm. Bull, 45, 584, 1997. 

A facile method for the synthesis of N-substituted 2-benzimidazolinones 142 has been developed by Romero et al. (96TL2361) using A-substituted ureas 139, which are cyclized to 142 with IBTA as an oxidant. The reaction probably proceeds via intermediates 140 and 141. Besides the iV-alkyl or aryl substituent, presence of the 1-methoxy group is necessary for the success of this cyclization. Another benzimidazoles synthesis involves cycli-zation of N-phenyl-C-alkyl formimidamides with IBD [95JCS(P1)615]... 

Ligand exchange provides a route for the synthesis of chiral A3-iodanes. [(+)-10-Camphorsulfonyl]oxy-A3-iodane 8 was prepared from the reaction of 4 with (+)-10-camphorsulfonic acid in aqueous acetonitrile [22]. Concentration of a solution of [methoxy(tosyloxy)iodo]benzene and (+)-menthol in dichloro-methane under vacuum results in facile ligand exchange on iodine to give the chiral A3-iodane 9 [23]. 

The additional presence of a 3-methoxy substituent on the benzyl group confers greater stability on the intermediate cation, and consequently oxidation of DMPM ethers by DDQ is even more facile. Yonemitsu and cowoikers have used this differential reactivity of substituted benzyl ethers to great effect in the total synthesis of the macrolide antibiotics methynolide, tylonolide, (95)-9-dihydroerythro-nolide and pikronolide. The pikronolide synthesis provides an excellent example of the selective, sequential deprotection of DMPM, MPM and benzyl ether protecting groups (Scheme 7). 

In the laboratory of R.A. Jones, A/ -methoxy derivatives of adenosine and 2 -deoxyadenosine were found to undergo a facile Dimroth rearrangement The high-yielding process allowed the efficient synthesis of [1,7- N2]- and [1,7, NH2- N3] adenosine and 2 -deoxyadenosine that are important tools in the NMR studies of nucleic acid structure and interactions. The rearrangement was carried out in weakly acidic refluxing methanol. 

A facile one-step synthesis " of ( )-cis- and trans-16-hydroxy-15-methoxy-erythrinanone (14 R = OMe, R = OH, X = O) and (15 R = OMe, R = OH, X = O) by the condensation of 2-(ethoxycarbonylmethyl)methylcyclo-hexanone with 3-hydroxy-4-methoxy-jS-phenethylamine in refluxing ethanol without acid catalysis, reported by Kametani and co-workers, has been discussed... 

An efficient synthesis of iV-ethyl-l-hydroxy-7-methoxymitosane (115) was reported by Verboom and co-workers [39, 40]. This synthesis was based on a variation of the Madelung reaction in which the cyclization to an indole was facilated by an electron-withdrawing cyano group on the benzylic carbon (Scheme 15). The starting material, 2-amino-5-methoxy-4-methylbenzonitrile (110), was treated with 4-chlorobutyryl chloride to give amide 111, which was... 

Ruthenium(II)-mediated oxidative annulation reaction of benzoic acids and cyclopropylarylethynes furnishes a mixture of 3- and 4-cyclopropyl substituted isocoumarins (130BC142).A facile one-pot synthesis of4-aryl-isocoumarins involves an acidic hydrolysis of ( -2-(l-aryl-2-methoxy-ethenyl)benzaldehydes with HBr and subsequent oxidation with PCC (13HCA2173). 

Carballeira, N.M., Emiliano, A Hernandez-Alonso, N., and Gonzalez, F.A. (1998) Facile total synthesis and antimicrobial activity of the marine fatty acids (Z)-2-metho3gr-5-hexadecenoic add and (Z)-2-methoxy-6-hexadecenoic acid. J. Nat. Prod., 61,1543-1546. 

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