STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VIII. β-SUBSTITUTED-Δ<sup>α,β</sup>-BUTENOLIDES OF THE NAPHTHALENE AND INDENE SERIES

Knowles, William S.; Kuck, J. A.; Elderfield, Robert C.

doi:10.1021/jo01198a011

Cited by 17 publications

(14 citation statements)

References 9 publications

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“…Chromatography on silicic acid gave three compounds. On elution with 2% ethanol in pentane, 1,3-diacetylindene (10b, 2.5 g, 15%) was obtained as an oil: ir (neat) 1750 (saturated ester C=0), 1680 cm-1 (conjugated ester C=0); nmr (CDCls) 7.5 (m, 1 H, aromatic), 7.1 (m, 3 H, aromatic), 6.7-6.4 (m, 2 H), 2.3 (s, 3 H, COCH3), 2.1 (s, 3 H, COCH3). Anal. Caled for Ci3H1202: C, 77.98; , 6.04.…”

Section: Methodsmentioning

confidence: 99%

“…Attempts to synthesize 6 through intermediates 10a, 7,5 and 86 were unsuccessful. By analogy, compound 7 should , be obtainable from 1-acetylindene and diethyl carbonate. 5 Reaction of 1-indenecarboxylic acid chloride7 with di-methylcadmium8 gave complex mixtures, while indenyl-lithium9 and acetyl bromide produced 10a (9%) along with 3,3-diacetylindene 9 and the isomeric 10b (15%) formed by further acetylation of 10a.…”

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confidence: 99%

“…The low yield of 10a coupled with the unstable nature of the compound led to investigations of other methods of synthesizing 7. Treatment of indenyllithium with monoethylmalonyl chloride10 in order to prepare 7 directly resulted in complex mixtures. Indenecarboxylic acid chloride on treatment with the magnesium salt of ethyl tert-butyl malonate11 gave ethyl tertbutyl 1-indenoylmalonate (11, 66%).…”

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Simplified analogs of lysergic acid. V. Derivatives of N,N-diethyl-1-methyl-9H-indeno-1,2,3,9a-tetrahydro[2,1-b]pyridine-3-carboxamide

Craig¹,

Dinner²,

Mulligan³

1974

J. Org. Chem.

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The synthesis of the simplified analog of lysergic acid diethylamide, !V,lV-diethyl-l-methyl-9.f/-indeno-l,2,3-9a-tetrahydro[2,l-6]pyridine-3-carboxamide (6b), in which the ß-arylethylamine moiety exists twice with reference to one benzene nucleus, is described. The starting material (indene) was converted to the tricyclic intermediate ethyl 4a-hydroxy-4-keto-l-methyl-9.fi-indeno-1,2,3,4,4a,9a-hexahydro[2,l-6]pyridine-3-carboxylate (28a) via a six-step sequence and thence to the title compound 6b in four steps. The stereochemistry of some of the key intermediates and of the final product is discussed.

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Section: Methodsmentioning

confidence: 99%

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Simplified analogs of lysergic acid. V. Derivatives of N,N-diethyl-1-methyl-9H-indeno-1,2,3,9a-tetrahydro[2,1-b]pyridine-3-carboxamide

Craig¹,

Dinner²,

Mulligan³

1974

J. Org. Chem.

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“…from Harvard in 1939, Knowles began doctoral studies at Columbia University (New York) under Robert Elderfield. Knowles' doctoral thesis focused on the synthesis of simple analogs of cardiac aglycones and testing of their cardiac activity (3,4). ''I was sort of a steroid chemist,'' he says.…”

Section: Drafted Into Industrymentioning

confidence: 99%

Profile of William S. Knowles

Yun¹

2005

Proc. Natl. Acad. Sci. U.S.A.

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“…3-Carboxy indan-1-one (4) and its 5: 6-dimethoxy derivative ( 5 ) were reduced to the corresponding carboxy acids by Clemmensen reduction (6,7).…”

Section: Scheme Imentioning

confidence: 99%

Synthesis and Pharmacology of Some Pyrroles and Indan Amines: Hexahydro Indeno (1,2-c) Pyrroles and Indan Amines

Lahiri

Pathak

1968

Journal of Pharmaceutical Sciences

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STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VIII. β-SUBSTITUTED-Δ^α,β-BUTENOLIDES OF THE NAPHTHALENE AND INDENE SERIES

Cited by 17 publications

References 9 publications

Simplified analogs of lysergic acid. V. Derivatives of N,N-diethyl-1-methyl-9H-indeno-1,2,3,9a-tetrahydro[2,1-b]pyridine-3-carboxamide

Simplified analogs of lysergic acid. V. Derivatives of N,N-diethyl-1-methyl-9H-indeno-1,2,3,9a-tetrahydro[2,1-b]pyridine-3-carboxamide

Profile of William S. Knowles

Synthesis and Pharmacology of Some Pyrroles and Indan Amines: Hexahydro Indeno (1,2-c) Pyrroles and Indan Amines

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STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VIII. β-SUBSTITUTED-Δα,β-BUTENOLIDES OF THE NAPHTHALENE AND INDENE SERIES

Cited by 17 publications

References 9 publications

Simplified analogs of lysergic acid. V. Derivatives of N,N-diethyl-1-methyl-9H-indeno-1,2,3,9a-tetrahydro[2,1-b]pyridine-3-carboxamide

Simplified analogs of lysergic acid. V. Derivatives of N,N-diethyl-1-methyl-9H-indeno-1,2,3,9a-tetrahydro[2,1-b]pyridine-3-carboxamide

Profile of William S. Knowles

Synthesis and Pharmacology of Some Pyrroles and Indan Amines: Hexahydro Indeno (1,2-c) Pyrroles and Indan Amines

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Product

Resources

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STUDIES ON LACTONES RELATED TO THE CARDIAC AGLYCONES. VIII. β-SUBSTITUTED-Δ^α,β-BUTENOLIDES OF THE NAPHTHALENE AND INDENE SERIES