Structures of pyridine and quinoline-n-oxides

Desiderato, R.; Terry, J. C.

doi:10.1016/s0040-4039(01)98430-8

Cited by 4 publications

(1 citation statement)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Except for a shortening of the C(15)-C(18) and C(3)-C(4) bonds as well as the C(methyl)-C(ring) bonds, the structural parameters compare well with those reported for the parent ellipticine (Courseille, Busetta & Hospital, 1974) and 5,6,11-trimethylpyrido-[4,3-b]carbazole (CourseiUe, Busetta & Pr~cigoux, 1981). The N-O bond distance and associated bond angles are comparable with those found for pyridine N-oxide (Desiderato & Terry, 1970). However, the N-O distance of 1.347 (4)A is longer than those found in compounds such as 2-{[(hydroxymethoxy)-methyl]thio }pyridine 1-oxide [ 1-319 (5) A] (Haugwitz, Toeplitz & Gougoutas, 1980), 6-chloro-3-ethoxycarbonyl-2-methylquinoxaline 1,4-dioxide [1.294(2) and 1.308 (2)A] (MacDonald & Arora, 1981) and others.…”

Section: C1~c~5~) Ow( 1 )supporting

confidence: 71%

5,11-Dimethyl-6H-pyrido[4,3-b]carbazole 2-oxide trihydrate (ellipticine N-oxide trihydrate), C17H14N2O.3H2O

Garlich¹,

Kaiser²,

Schlemper³

1984

Acta Crystallogr C

View full text Add to dashboard Cite

Section: C1~c~5~) Ow( 1 )supporting

confidence: 71%

5,11-Dimethyl-6H-pyrido[4,3-b]carbazole 2-oxide trihydrate (ellipticine N-oxide trihydrate), C17H14N2O.3H2O

Garlich¹,

Kaiser²,

Schlemper³

1984

Acta Crystallogr C

View full text Add to dashboard Cite

Preparation of the HIV Attachment Inhibitor BMS-663068. Part 5. Selective C-7 Bromination of the 6-Azaindole Core

González‐Bobes

Hickey

Cohen

et al. 2017

Org. Process Res. Dev.

View full text Add to dashboard Cite

We report research focused on the preparation of an advanced intermediate in the synthesis of a novel antiretroviral. This manuscript describes the development of an efficient oxidation of a 6-azaindole derivative, the bromination of the resulting N-oxide using PyBroP, the removal of the protecting group, and the isolation of the brominated azaindole product. The work reported herein has been successfully implemented in the multikilogram scale to fund development and clinical activities of BMS-663068.

show abstract

Phase-Vanishing Methodology for Efficient Bromination, Alkylation, Epoxidation, and Oxidation Reactions of Organic Substrates

2003

View full text Add to dashboard Cite

[reaction: see text] In cases where both reactants in a phase-vanishing reaction are less dense than the fluorous phase, an alternative to the U-tube method is to employ a solvent with greater density than the fluorous phase, such as 1,2-dibromoethane. This modification has been successfully applied to the methylation of a phenol derivative with dimethyl sulfate and to the m-CPBA-induced epoxidation of alkenes, N-oxide formation from nitrogen-containing compounds, and S-oxide or sulfone formation from organic sulfides.

show abstract

Structures of pyridine and quinoline-n-oxides

Cited by 4 publications

References 3 publications

5,11-Dimethyl-6H-pyrido[4,3-b]carbazole 2-oxide trihydrate (ellipticine N-oxide trihydrate), C17H14N2O.3H2O

5,11-Dimethyl-6H-pyrido[4,3-b]carbazole 2-oxide trihydrate (ellipticine N-oxide trihydrate), C17H14N2O.3H2O

Preparation of the HIV Attachment Inhibitor BMS-663068. Part 5. Selective C-7 Bromination of the 6-Azaindole Core

Phase-Vanishing Methodology for Efficient Bromination, Alkylation, Epoxidation, and Oxidation Reactions of Organic Substrates

Contact Info

Product

Resources

About