The application of lithium aluminium hydride to the preparation of some amino-alkanols

Avison, A. W. D.

doi:10.1002/jbt.2570011009

Cited by 1 publication

(2 citation statements)

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“…The combined product was rinsed with water and dried in vacuo over Drierite. This product was presumed to be mostly the bis keto acid (15) and appeared to be contaminated with succinic acid.…”

Section: Methodsmentioning

confidence: 99%

“…Azulene was treated with an excess of succinic anhydride under Friedel-Crafts conditions. The bis keto acid disubstitution product (15) was difficult to purify and clean separation from succinic acid was obtained only after esterification to form the bis keto ester (16). Despite the trial of many different reaction conditions, the best yield of 16 obtained was 15%.…”

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confidence: 99%

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Synthesis of azulene-1-alkanoic acids, azulene-1,3-dialkanoic acids, and related compounds. A 1,3-bridged azulene

Anderson¹,

Breazeale²

1969

J. Org. Chem.

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1,3-Bis(2',2'-dicarboxyethyl)azulene (2), azulyl-1,3-bis(propanoic acid) (3), 1,3-bis(2'-carbethoxy-3'-oxo-buty1)azulene (4), 1,3-bis(3'-oxobutyl)azulene (S), diethyl azulene-l,&dipropanoate (6), and l,&bis(3'-hy-droxypropy1)azulene (7) have been synthesized via nucleophilic displacement reactions on azulyl-l,3-bis(meth~ltrimethylammonium) diiodide ( 1). Vilsmeier acylation reactions and reduction of the carbonyl groups in the 1-acylazulene products to methylenes by either the hydride reduction-alkylideneazulenium salt-hydride reduction method or, in one step, by diborane have been used to prepare I-ethylazulene, ethyl 5-(1-azulyl)-5oxopentanoate (sa), ethyl 5-( 1-azuly1)pentanoate (loa), 1-(1'-oxo-4'-carbethoxybutyl)-3-(5'-chloropentyl)azulene (1 la), azulene-1,3-bis(hexanenitrile) (14a), ethyl 4-( l-azulyl)-4-oxobutanoate (8b), 1-(4'-chlorobuty1)-3-(1'-oxo-3'-carbethoxypropyl)azulene (llb), azulene-l,3-bis(pentanenitrile) (14b), 1,3-bis(l'-oxo-3'-carbo-methoxypropy1)azulene (16), N,N-diethyl-10-( 1-azuly1)decanamide (21), pentylazulene (22), 1,3-dipentylazulene (23), 1,3-dipropionylazulene (24), and 1,3-dipropylazulene (25). The principal maxima in the visible absorption spectra for the 1-alkyl-and 1,3-dialkylazulenes are compared. The diborane reduction of the acylazulenes is discussed. A high-dilution Thorpe-Ziegler ring closure of 14a gave 1,3-(5'-cyano-6'-oxoundeca-met8hylene)azulene (26), the first example of a l13-bridged azulene. Attempts to form l,&bridged products from 14b, 21, and 6 were unsuccessful. (1965), and preceding papers.for certain cases, the reaction with aliphatic diazo compounds.' The former had provided the first step in pathways to azulene-1-ethanoic acid and azulene-lpropanoic acidP4 and the latter afforded a direct route to ethyl azulene-1-ethanoate. Since the results of an attempt to form an azulene-1,3-dialkanoic acid ester by the acid-catalyzed decomposition of an w-diazo ester in the presence of azulene were not promising, the displacement reactions of azulyl-l,3-bis(methyltrimethylammonium) diiodide (1) with the anions of active methylene compounds were tried (Scheme I). From 1 and diethyl sodiomalonate was obtained, after hydroly-

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%