Conformation analyses, dynamic behavior, and amide bond distortions of medium-sized heterocycles. 2. Partially and fully reduced 1-benzazocines, benzazonines, and benzazecines

Journal of Organic Chemistry

Volumn 70, Issue 5, 2005, Pages 1552-1557

  Qadir, Maryiam ^a   Cobb, Jonathan ^a   Sheldrake, Peter W ^b,e   Whittall, Neil ^b   White, Andrew J P ^c   King, Kuok Hii ^c   Horton, Peter N ^d   Hursthouse, Michael B ^d  

^a KING'S COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c IMPERIAL COLLEGE LONDON   (United Kingdom)

^d UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^e INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL BONDS; NITROGEN; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

DYNAMIC BEHAVIOR; RING STRAINS; STABLE STRUCTURES; TRANSANNULAR DISTANCES;

ORGANIC COMPOUNDS;

1 BENZOYL 1,2,3,4,5,6 HEXAHYDRO 1H 1 BENZAZOCINE; 1 BENZOYL 1,2,3,4,5,8 TETRAHYDRO 1H 1 BENZAZECINE; 1 BENZOYL 1,2,3,6 TETRAHYDRO 1 BENZAZOCINE; 1 BENZOYL 2,3,4,5,6,7 HEXAHYDRO 1H 1 BENZAZONINE; 1 BENZOYL 2,3,4,7 TETRAHYDRO 1H 1 BENZAZONINE; 1 BENZYL 1,2,3,4,5,6 HEXAHYDRO 1 BENZAZOCINE; 1 BENZYL 2,3,4,5,6,7 HEXAHYDRO 1H 1 BENZAZONINE; BENZAZOCINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; MATHEMATICAL ANALYSIS; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMIDES; AZO COMPOUNDS; AZOCINES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HETEROCYCLIC COMPOUNDS, 2-RING; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP; TEMPERATURE;

EID: 14544304543     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048117j     Document Type: Article

References (5)

1. (a) Shiraishi, M.; Baba, M.; Aikawa, K.; Kanzaki, N.; Seto, M.; Iizawa, Y. Preparation of 1-benzazocine-5-carboxamides and related bicyclic compounds as CCR-5 antagonists for use against HIV infection and other diseases. World Patent WO2003/014105, 2003.
2. (b) Hamminga, D.; van Wjingaarden, I.; Jansen, J. W. C. M. Preparation of 8,9-annelated-1,2,3,4-tetrahydro-β-carboline derivatives as fibrinolytics. European Patent EP380155, 1990.
3. Alder, R. W.; White, J. M. In Conformational Analysis of Medium-Sized Heterocycles; Glass, R. S., Ed.; VCH: New York, 1988; Chapter 3.
4. The yields of the N-alkylation reactions were poor if they were performed after the Stille reaction, presumbly due to reduced electrophilicity of these alkenyl tosylates.
5. Benzoazecine 5c was not hydrogenated due to the small quantity available.