The Synthesis of Heterocyclic Systems from Cyclohepta-2,6-dienone

Kashman, Yoel; Cherkez, S.

doi:10.1055/s-1974-23468

Cited by 10 publications

(9 citation statements)

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“…(C9H19N20C1) C, , N, Cl. 6.7-Dimethyl-6,7-diazabicyclo[3.2.2]non-3a-yl Tropate (1). A mixture of 9.8 g (58 mmol) of 6,7-dimethyl-6,7-diazabicyclo-[3.2.2]nonan-3a-ol hydrochloride and 14.5 g (64 mmol) of acetyltropoyl chloride5 was heated for 4 h at 80 °C.…”

Section: Methodsmentioning

confidence: 99%

“…One gram (4.8 mmol) of 6,7-dimethyl-6,7-diazabicyclo[3.2.2]nonan-3/3-ol hydrochloride was reacted with acetyltropoyl chloride as described for 1, yielding 0.6 g (40%) of 4: NMR (CDCla) 1.59-1.99 (m, C89-H, 4 ), 1.99-2.30 (m, C24-H, 4 H), 2.52 (s, NCH3, 3H), 2.54 (s, NCH3, 3H), 2.94 (m, Cli5-H, 2H), 3.71-4.27 (ABC, CHCH2OH, 3 H), 5.28 (quin, J = 8.8 Hz, C3-H), 7.31 (m, Ph, 5 H); IR (neat) 3700-3000, 2950, 2880, 2800, 1730, (C=0), 1500, 1460,1360, 1170,1050, 975, 707 cm"1; MS (m/e) 318 (M+, 100), 303 (M+ -CHa, 100), 288.7 (m*, 318 -303), 153 (21). 6.7-Dimethyl-6,7-diazabicyclo[3.2.2]non-3|S-yl Tropate Methiodide (5).…”

Section: Methodsmentioning

confidence: 99%

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Structure-activity relationship in a new series of atropine analogs. 1. N,N'-Disubstituted 6,7-diazabicyclo[3.2.2]nonane derivatives

Cherkez¹,

Yellin²,

Kashman³

et al. 1979

J. Med. Chem.

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The synthesis of a new series of N,N'-disubstituted 6,7-diazabicyclo[3.2.2]nonane derivatives is described. The antimuscarinic potency of these drugs was evaluated in the guinea pig ileum and compared to that of atropine sulfate. All the drugs tested competitively inhibited the acetylcholine-induced contractions. Kd values were calculated and, in several cases, compared to those obtained by direct binding to the muscarinic receptor from mouse brain. The order of potencies followed that which is known for various tropine and pseudotropine esters; that is, the 3alpha configuration is more potent than the 3beta configuration, and the quaternary analogues are more potent than the tertiary ones. The antimuscarinic activity of the drugs is dicussed in terms of their acetylcholine-like molecular arrangement that gives rise to a characteristic interaction pharmacophore.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Structure-activity relationship in a new series of atropine analogs. 1. N,N'-Disubstituted 6,7-diazabicyclo[3.2.2]nonane derivatives

Cherkez¹,

Yellin²,

Kashman³

et al. 1979

J. Med. Chem.

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“…The well-known three-component coupling of butanedial ( 18 ), acetone-1,3-dicarboxylic acid ( 20 ), and MeNH 2 reported by Robinson constituted the first synthesis of tropinone, providing the compound in 42% yield . Tropinone has also been prepared by the addition of MeNH 2 to cycloheptadienone . A drawback to the development of this preparation is that cycloheptadienone is commercially unavailable and requires a minimum of two steps from cycloheptanone …”

Section: Resultsmentioning

confidence: 99%

Development of a Manufacturing Process for Zatosetron Maleate

Burks¹,

Espinosa²,

Labell³

et al. 1997

Org. Process Res. Dev.

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Zatosetron maleate is a potent, selective 5-hydroxytryptamine receptor antagonist. In anticipation of commercialization, a manufacturing synthesis of zatosetron from tropinone and 5-chlorosalicylic acid was developed. Development efforts focused on addressing several key issues including the supply and quality of the critical raw material tropinone, improvements in the stereoselective formation of 3-endo-tropanamine, and the compatibility with existing manufacturing capabilities of process requirements for the Claisen rearrangement used to produce a crucial benzofuran intermediate. The results of these studies and an improved route to zatosetron maleate are described.

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“…Further reaction with an excess of a Michael acceptor produces diaddition products in excellent yields 69 . Sequential additions of hydroxylamine to endocyclic double bonds such as in 41 have also been applied for preparation of bridged heterocyclic systems of type 42 (equation 28) 110 . Addition of hydroxylamines to an endocyclic bond is possible if the double bond is a part of an aromatic heterocyclic system (e.g.…”

Section: E Nucleophilic Addition Of Hydroxylamines To Activated C=c mentioning

confidence: 99%

Synthesis of Hydroxylamines

Melman

2010

Patai's Chemistry of Functional Groups

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Introduction Hydroxylamines through Hydrolysis of Hydroxamic Acids, Oximes and Nitrones Synthesis of Hydroxylamines through Alkylation and Arylation of other Hydroxylamines Hydroxylamines through Reduction Reactions Hydroxylamines through Addition to the C  N Double Bond of Oximes, Oxime Ethers and Nitrones Hydroxylamines through Addition to the N  O Double Bond of Nitroso and Nitro Compounds Hydroxylamines through Oxidation of Amines Hydroxylamines through Cycloaddition Reactions

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The Synthesis of Heterocyclic Systems from Cyclohepta-2,6-dienone

Cited by 10 publications

References 0 publications

Structure-activity relationship in a new series of atropine analogs. 1. N,N'-Disubstituted 6,7-diazabicyclo[3.2.2]nonane derivatives

Structure-activity relationship in a new series of atropine analogs. 1. N,N'-Disubstituted 6,7-diazabicyclo[3.2.2]nonane derivatives

Development of a Manufacturing Process for Zatosetron Maleate

Synthesis of Hydroxylamines

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