AZABICYCLOALKANES. 2-AZABICYCLO[3·3·1]NONANE<sup>1,2</sup>

Cronyn, Marshall W.

doi:10.1021/jo01158a009

Cited by 20 publications

(4 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N-Methylation with NaH-CH3I gave 2-methyl-2-azabicyclo[3.3.1]nonan-3-one, as described by Dygos. 16 The latter lactam was converted to the desired 7 with LiAlH4 by the method of Dygos16 and isolated as its picrate salt, mp 262-264 °C dec (lit.16 262-263 °C dec).…”

Section: Methodsmentioning

confidence: 99%

“…The isomeric nature of 3 and 6 was further confirmed by the fact that upon catalytic hydrogenation both compounds were converted to 2-methyl-2-azabicyclo-[3.3.1]nonane (7, Scheme I) which was identical (as their picrate salts) with authentic 7 prepared by an unambiguous route from m-nitrophenylacetic acid. 16 Biological Results. The analgetic activities of 3-6 were determined in mice by the hot-plate method17 and compared with several benzomorphan compounds as indicated in Table I.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Azabicyclo chemistry. 6. An investigation of one of the chemical parameters for analgetic activity. Synthesis of 2-methyl-2-azabicyclo[3.3.1]non-6-ene and -non-7-ene

Cavestri¹,

Mokotoff²

1977

J. Med. Chem.

View full text Add to dashboard Cite

The olefins 2-methyl-2-azabicyclo[3.3.1]non-6-ene (3) and -non-7-ene (6) were prepared in order to evaluate their analgetic activity. The reduction of 2-methyl-2-azabicyclo[3.3.1]nonan-7-one (4) with NaBH4 gave, stereospecifically, the axial alcohol 5. Reaction of 5 with CH3SO2Cl-pyridine gave directly the olefins 3 and 6, both of which upon hydrogenation gave the known 2-methyl-2-azabicyclo[3.3.1]nonane (7). The structural proof of 3, 5, and 6 was ascertained by spectral methods. Of the compounds prepared, 3, 5, and 6 were essentially inactive as analgetics when tested in mice by the hot-plate method, while 4 had marginal activity.

show abstract

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Azabicyclo chemistry. 6. An investigation of one of the chemical parameters for analgetic activity. Synthesis of 2-methyl-2-azabicyclo[3.3.1]non-6-ene and -non-7-ene

Cavestri¹,

Mokotoff²

1977

J. Med. Chem.

View full text Add to dashboard Cite

show abstract

“…We first examined this approach on cage structure 44 (Scheme ). Treatment of 44 with boron tribromide in dichloromethane gave alcohol 108 in 75% yield . A Swern oxidation proceeded smoothly to afford aldehyde 109 in 92% yield …”

Section: Introductionmentioning

confidence: 99%

Free Radical Cyclizations in Alkaloid Total Synthesis: (±)-21-Oxogelsemine and (±)-Gelsemine

Atarashi

Choi

et al. 1997

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Total syntheses of (±)-21-oxogelsemine (3) and (±)-gelsemine (1) are described. Free radical cyclizations play important roles in constructing the tricyclic core (40 → 41) and oxindole (93 → 96) substructures of the target alkaloids, and an isomerization−cyclization strategy (101 → 102) was used to complete construction of the gelsemine cage. Observations made along the way include intramolecular 1,4- and 1,6-hydrogen atom transfers (64 → 65 and 40 → 47) and a free radical cyclization-fragmentation sequence (85 → 86 + 87). A retroaldol−aldol strategy for adjusting oxindole stereochemistry in gelsemine-like structures is also described (72 → 74 and 86 → 87).

show abstract

“…Finally, it was found that the conversion could be effected simply by shaking 1 Since the completion of this work (1948), the reduction of a cyclic thioamide by means of Raney nickel has been reported (18). A brief report of the action of Raney nickel on certain other thioamides has also appeared (19).…”

mentioning

confidence: 93%

Raney Nickel Hydrogenolysis of Thioamides: A New Amine Synthesis

Kornfeld¹

1951

J. Org. Chem.

View full text Add to dashboard Cite

AZABICYCLOALKANES. 2-AZABICYCLO[3·3·1]NONANE^1,2

Cited by 20 publications

References 10 publications

Azabicyclo chemistry. 6. An investigation of one of the chemical parameters for analgetic activity. Synthesis of 2-methyl-2-azabicyclo[3.3.1]non-6-ene and -non-7-ene

Azabicyclo chemistry. 6. An investigation of one of the chemical parameters for analgetic activity. Synthesis of 2-methyl-2-azabicyclo[3.3.1]non-6-ene and -non-7-ene

Free Radical Cyclizations in Alkaloid Total Synthesis: (±)-21-Oxogelsemine and (±)-Gelsemine

Raney Nickel Hydrogenolysis of Thioamides: A New Amine Synthesis

Contact Info

Product

Resources

About

AZABICYCLOALKANES. 2-AZABICYCLO[3·3·1]NONANE1,2

Cited by 20 publications

References 10 publications

Azabicyclo chemistry. 6. An investigation of one of the chemical parameters for analgetic activity. Synthesis of 2-methyl-2-azabicyclo[3.3.1]non-6-ene and -non-7-ene

Azabicyclo chemistry. 6. An investigation of one of the chemical parameters for analgetic activity. Synthesis of 2-methyl-2-azabicyclo[3.3.1]non-6-ene and -non-7-ene

Free Radical Cyclizations in Alkaloid Total Synthesis: (±)-21-Oxogelsemine and (±)-Gelsemine

Raney Nickel Hydrogenolysis of Thioamides: A New Amine Synthesis

Contact Info

Product

Resources

About

AZABICYCLOALKANES. 2-AZABICYCLO[3·3·1]NONANE^1,2