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. 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).

scholarly journals Oxidation Reactions of Marchantin A Trimethyl Ether and Some Aromatic Compounds using m-Chloroperbenzoic Acid. Formation of Muconic Acid Ester and m-Chlorobenzoate

1999 ◽  
Vol 23 (8) ◽  
pp. 470-471
Author(s):  
Motoo Tori ◽  
Masakazu Sono ◽  
Keiko Takikawa ◽  
Reiko Matsuda ◽  
Masao Toyota ◽  
...  
Keyword(s):  
Aromatic Ring ◽  
Methyl Ether ◽  
Aromatic Compounds ◽  
Acid Ester ◽  
Acid Formation ◽  
Oxidation Reactions ◽  
Muconic Acid ◽  
Trimethyl Ether

On treatment with m-chloroperbenzoic acid, dihydroeugenol methyl ether and marchantin A trimethyl ether afford muconic acid ester derivatives by oxidation of the aromatic ring as well as hydroxylated derivatives; the m-chlorobenzoate of the dihydroeugenol derivative is also observed for the former.

Enantioselective Organocatalytic Construction of Carbocycles: The Nicolaou Synthesis of Biyouyanagin A

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Methyl Ether ◽  
Conjugate Addition ◽  
Unsaturated Aldehyde ◽  
Enantiomerically Pure ◽  
Intramolecular Alkylation ◽  
Stereogenic Centers ◽  
Chinese Academy Of Sciences ◽  
Academy Of Sciences ◽  
Polycyclic System ◽  
Selective Addition

One of the more powerful routes to enantiomerically-pure carbocycles is the desymmetrization of a prochiral ring. Karl Anker Jørgensen of Aarhus University has found (J. Am. Chem. Soc. 2007, 129, 441) that many cyclic β-ketoesters, including the vinylogous carbonate 1, can be homologated with 2 to the corresponding alkyne 3, in high ee. Sanzhong Luo of the Chinese Academy of Sciences, Beijing, and Jin-Pei Cheng, of the Chinese Academy of Sciences and Nankai University, have shown (J. Org. Chem. 2007, 72, 9350) that the catalyst 6 mediated the selective addition of 4-substituted cyclohexanones such as 4 to the nitroalkene 5, establishing three new stereogenic centers. Organocatalysts, alone or complexed with activating metals, have also been used to effect enantioselective ring construction. E. J. Corey of Harvard University has established (J. Am. Chem. Soc. 2007, 129, 12686) that the proline-derived complex 10 will mediate the 2 + 2 addition of a cyclic enol ether with an acrylate to give the cyclobutane 11. Further elaboration led to the cyclohexenone 12. Armando Córdova of Stockholm University has described (Tetrahedron Lett. 2007, 48, 5835) a novel route to cyclopentanones such as 16, via tandem conjugate addition/intramolecular alkylation. Professor Jørgensen has reported (Angew. Chem. Int. Ed . 2007, 46 , 9202) the double addition of 18 to the unsaturated aldehyde 17 to give 20. Earlier last year, Yujiro Hayashi of the Tokyo University of Science had shown (Angew. Chem. Int. Ed. 2007, 46, 4922) that the double addition of the inexpensive 21 to 5 could, depending on conditions, be directed selectively to 22, 23, or 24. As illustrated by the conversion of 8 to 13, organocatalysis can be used to effect the enantioselective construction of polycarbocyclic products. The initial ring prepared in enantiomerically-pure form by organocatalysis can also set the chirality of a polycyclic system. Professor Corey has reported (J. Am. Chem. Soc. 2007, 129, 10346) that Itsuno-Corey reduction of the prochiral diketone 25 led to the ketone 27. Cyclization followed by oxidation and reduction then delivered estrone methyl ether 28.

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. II. The preparation of intermediates for diterpene synthesis by intramolecular carbenoid addition reactions

1972 ◽  
Vol 25 (1) ◽  
pp. 137 ◽  
Author(s):  
DJ Beames ◽  
JA Halleday ◽  
LN Mander
Keyword(s):  
New Method ◽  
Addition Reactions ◽  
Dilute Acid ◽  
Ring Systems ◽  
Intramolecular Alkylation ◽  
Tricyclic Compounds ◽  
Cyclopropyl Ketones ◽  
Diazomethyl Ketones

A new method is described for the preparation of tricyclic compounds containing the 3,2,1- and 2,2,2-bicyclooctane ring systems. The copper-catalysed decomposition of the diazomethyl ketones derived from the olefinic acids (7), (9), (18), and (19) afforded, respectively, the cyclopropyl ketones (12), (13), (21), and (20). These compounds were transformed into the cyolopropyl diketones (15) and (22) which by treatment with dilute acid or base gave, in turn, the bridged octalones (1) and (2).

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).

The First Facile Synthesis of Some 1,2a,3,8b-Tetrahydro-2H-Cyclobuta[c] Chromenes Through Intramolecular Alkylation of an Aromatic Ring by a Cyclobutanone

Synlett ◽  
2002 ◽  
Vol 2002 (05) ◽  
pp. 0796-0798 ◽  
Author(s):  
Angela M. Bernard ◽  
Costantino Floris ◽  
Angelo Frongia ◽  
Pier P. Piras
Keyword(s):  
Aromatic Ring ◽  
Facile Synthesis ◽  
Intramolecular Alkylation
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