Studies on intramolecular alkylation. X. The acid-catalysed reactions of 5,8-Dialkoxy-1,2,3,4-tetrahydronaphthyl diazomethyl ketones

1978 ◽  
Vol 31 (7) ◽  
pp. 1561 ◽  
Author(s):  
DW Johnson ◽  
LN Mander
Keyword(s):  
Trifluoroacetic Acid ◽  
Acid Treatment ◽  
Polyphosphoric Acid ◽  
Intramolecular Alkylation ◽  
Naphthoic Acid ◽  
Acid Catalysed Reactions ◽  
Diazomethyl Ketones

5,8-Dimethoxy-3,4-dihydronaphthalen-1(2H)-one was converted into diazomethyl 5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthyl ketone (10) which, when treated with trifluoroacetic acid at 0°, gave 5,8- dimethoxy-4,4a-dihydro-3,4a-ethanonaphthalen-2(3H)-one (13), but at -15° gave 8-methoxy-1,2,3,4-tetrahydro-3,4a-ethanonaphthalene- 5(4aH),10-dione (14). 6-Methoxy-3,4-dihydronaphtha-len-1(2H)-one reacted with m-chloroperoxybenzoic acid to give 4,5-dihydro-1-benzoxepin-2(3H)-one (15) which after hydrolysis, ethylation and polyphosphoric acid treatment gave 5-ethoxy-8-methoxy-3,4-dihydronaphthalen-1(2H)-one (17). This compound was transformed into 5-ethoxy-8-hydroxy-1,2,3,4-tetrahydro-2-naphthoic acid (19) and thence to the ethoxy analogue of (14).

Studies on intramolecular alkylation. VI. ortho-Alkylation in phenolic diazoketones: the preparation of intermediates containing the Cyclohexa-2,4-dienonemoiety suitable for gibberellin synthesis

1974 ◽  
Vol 27 (6) ◽  
pp. 1277 ◽  
Author(s):  
DW Johnson ◽  
LN Mander
Keyword(s):  
Intramolecular Alkylation ◽  
Naphthoic Acid ◽  
Acid Catalysed Reactions

Simple efficient syntheses of 8-hydroxy- and 8-methoxy-2-tetralones (9) and (10), 1,2,3,4-tetrahydro-8- hydroxy-2-naphthoic acid (5), 1,2,3,4-tetrahydro-2-hydroxy-8-methoxy-2-naphthoic acid (8), 1,2,3,4-tetrahydro-2,s-dihydroxy-2-naphthoic acid (7) and 1,2,3,4-tetrahydro-5-hydroxy-2-naphthoic acid (20) are described. The acid-catalysed reactions of the diazoketones derived from (5) and (20) gave good yields of tricyclic ketones (3) and (4) incorporating a cyclohexa-2,4-dienone moiety. The potential of (3) for gibberellin synthesis is examined.

Studies on intramolecular alkylation. V. Intramolecular alkylation of the aromatic ring in tetrahydronaphthyl diazomethyl ketones

1974 ◽  
Vol 27 (6) ◽  
pp. 1269 ◽  
Author(s):  
DJ Beames ◽  
TR Klose ◽  
LN Mander
Keyword(s):  
Aromatic Ring ◽  
Methyl Ether ◽  
Intramolecular Alkylation ◽  
Acid Catalysed Reactions ◽  
Diazomethyl Ketones

The acid-catalysed reactions in weakly nucleophilic environments of 2-diazoacetyl-l,2,3,4-tetrahydronaphthalene (ll), of 6-diazoacetyl-5,6,7,8-tetrahydro-2-naphthol (2), of 6-diazoacetyl-5,6,7,8- tetrahydro-2-naphthyl methyl ether (3) and its 2,8 and 2,5 isomers (14) and (17), and of 6-diazo- acetyl-5,6,7,8-tetrahydro-6-trifluoroacetoxy-2-naphthyl methyl ether (9) have been studied. Several of the spirocyclohexa-2,5-dienone derivatives prepared thus, (4), (8) and (16), provide potential intermediates or models for the synthesis of tetracyclic diterpenoids.

Studies on intramolecular alkylation. XIV. The preparation of methoxylated cyclohexadienone derivatives from intramolecular diazoketone cyclizations inrelationship to isoquinoline alkaloid synthesis

1981 ◽  
Vol 34 (6) ◽  
pp. 1243 ◽  
Author(s):  
DW Johnson ◽  
LN Mander ◽  
TJ Masters
Keyword(s):  
Trifluoroacetic Acid ◽  
Isoquinoline Alkaloid ◽  
Intramolecular Alkylation ◽  
Alkaloid Synthesis ◽  
Tricyclic Compounds ◽  
Wide Range ◽  
Diazomethyl Ketones

A series of di- and tri-methoxytetrahydronaphthyl diazomethyl ketones (4), (6), (8), (25) and (27) have been prepared and cyclized in trifluoroacetic acid. A wide range of methoxylated cyclohexa- dienone containing tricyclic compounds (12), (15), (17), (18) and (30) were obtained as well as several rearranged derivatives, i.e. (13), (14), (32) and (33).

Synthesis of 1,1,5,6-Tetramethyl- and 7-Isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene

1999 ◽  
Vol 64 (3) ◽  
pp. 527-532 ◽  
Author(s):  
Ramchandra Bhimrao Mane ◽  
Abhijit Jaysingrao Kadam ◽  
Rajashree Sandeep Salunkhe
Keyword(s):  
Trifluoroacetic Acid ◽  
Polyphosphoric Acid ◽  
Titanium Tetrachloride ◽  
Grignard Reaction ◽  
Butanoic Acid ◽  
Methylmagnesium Iodide

4-(2,3-Dimethylphenyl)butanoic acid (4) was treated with excess of methyllithium to yield 5-(2,3-dimethylphenyl)-2-methylpentan-2-ol (6) which was cyclodehydrated using Dowex 50W-X8 resin, trifluoroacetic acid or polyphosphoric acid (PPA) to furnish 1,1,5,6-tetramethyl-1,2,3,4-tetrahydronaphthalene (1). The acid 4 was cyclized with PPA to furnish 5,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (5) which was converted into 1 by reaction with dimethylzinc and titanium tetrachloride. 4-(4-Isopropylphenyl)butanoic acid (7) on esterification followed by Grignard reaction with methylmagnesium iodide furnished 5-(4-isopropylphenyl)-2-methylpentan-2-ol (9), which was cyclodehydrated as above to yield 7-isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (2).

scholarly journals SYNTHESIS AND REACTIONS OF 1-(4’-BROMOPHENACYL)-3-(4’-BROMO-PHENYL)-4,6-DIMETHOXYINDOLE

2010 ◽  
Vol 5 (2) ◽  
pp. 156-162
Author(s):  
Jumina Jumina
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Trifluoroacetic Acid ◽  
Boron Trifluoride ◽  
Polyphosphoric Acid ◽  
Glacial Acetic Acid ◽  
Boron Trifluoride Etherate ◽  
Phosphoryl Chloride ◽  
Acetyl Ester ◽  
Toluenesulfonic Acid

  1-Phenacyl-3-aryl-4,6-dimethoxyindoles 2b and 2c were obtained in good yields respectively through cyclization of N,N-diphenacylaniline 1b and 1c in trifluoroacetic acid. However, instead of giving pyrroloindole 3c, treatment of phenacylindole 2c with polyphosphoric acid afforded indolizine 5 in 42% yield. Phenacylindole 2c reacts with the Vilsmeier aroylation reagent consisted of a mixture of phosphoryl chloride and p-chloro-N,N-dimethylbenzamide to give 2-aroylindole 6 (32%) and pyrroloindole 7 (22%). When treated with sodium borohydride, phenacylindole 2c gave alcohol 8 in 83% yield. Nonetheless, treatment of alcohol 8 with either p-toluenesulfonic acid in glacial acetic acid or boron trifluoride etherate in benzene did not give the desired dihydropyrroloindole 12. Instead, the reactions afforded respectively acetyl ester 9 and indole 10 in 56% and 63% yield.   Keywords: phenacylindole, aroylindole, pyrroloindole, and indolizine.

Studies on intramolecular alkylation. I. The preparation of tricyclic intermediates for the synthesis of diterpene alkaloids

1971 ◽  
Vol 24 (2) ◽  
pp. 343 ◽  
Author(s):  
DJ Beames ◽  
LN Mander
Keyword(s):  
Diterpene Alkaloids ◽  
Intramolecular Alkylation ◽  
Standard Procedures ◽  
Naphthoic Acid ◽  
Diastereomeric Mixture

The tricyclic dienones (14), (16), and (16) have been prepared by the Ar1-6 cyclization of a diastereomeric mixture of 7-[(2?-bromo-1?- tetrahydropyranyloxy)-ethyl]-5,6,7,8-tetrahydro-2-naphthols (11) and of 7-diazoacetyl-5,6,7,8-tetrahydro-2-naphthol (17). Intermediates (11) and (17) were prepared by standard procedures from 1,2,3,4-tetrahydro- 7-hydroxy-2-naphthoic acid.

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