Synthesis of some 2,5-benzoxazocine and 2,6-benzoxazonine derivatives from ω-(Dihydroisoindol-2-yl)alkanol precursors by means of cyanogen bromide

1982 ◽  
Vol 35 (11) ◽  
pp. 2307 ◽  
Author(s):  
JB Bremner ◽  
N Thirasasana
Keyword(s):  
Cyanogen Bromide ◽  
Ring Systems ◽  
Derivatives Of ◽  
Medium Ring ◽  
Moderate Yield

Reaction of cyanogen bromide with 2-(1-phenyl-2,3-dihydro-1H-isoindol-2-yl)ethanol (5a) gave 1-phenyl-3,4,5,6-tetrahydro-1H-2,5-benzoxazocine-5-carbonitrile (6a) in a low to moderate yield. Similarly, 3-(1-phenyl-2,3-dihydro-1H-isoindol-2-yl)propan-1-ol (5c) gave 1-phenyl-1,3,4,5,6,7-hexa-hydro-2,6-benzoxazonine-6-carbonitrile (6c). The analogous 1-(4-methoxyphenyl) derivatives of both medium ring systems were also prepared, and some mechanistic aspects of the results are discussed. Conversion of (6a) into the analgesic, Nefopam,is described.

Synthesis of 4H-Thieno[2,3-d]azonine and Thieno[2,3-d]azecine derivatives

1984 ◽  
Vol 37 (2) ◽  
pp. 367 ◽  
Author(s):  
EJ Browne
Keyword(s):  
Magnesium Oxide ◽  
Cyanogen Bromide ◽  
Functional Group ◽  
Cyclic Ketones ◽  
Ring Systems ◽  
Phenyl Derivative ◽  
Derivatives Of ◽  
Medium Ring

Derivatives of two new thieno medium-ring heterocyclic systems have been prepared by ring degradation using cyanogen bromide-induced solvolysis of tricyclic bases. Reaction of a hexahydrothieno[2,3-glindolizine (4a) and a hexahydro-7H-thieno[3,2-a]quinolizine (4b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of hexahydro-4H-thieno[2,3-d]azonine (5a) (6a) and octahydrothieno[2,3-d]azecine (5b) (6b), respectively. Functional group interconversions of these medium-ring systems are described, including oxidations to cyclic ketones. The 9a-phenyl derivative of (4a) reacted similarly. By contrast 10b-phenyl derivatives (10a,b) of a hexahydropyrrolo[2,1-a]isoquinoline reacted under these conditions to give medium-ring elimination products, derivatives of tetrahydro-1H-3-benzazonines.

Synthesis of Benzo[D]Thieno[2,3-G]Azecine and Benzo[D][1]Benzothieno[2,3-G]Azecine Derivatives

1986 ◽  
Vol 39 (5) ◽  
pp. 783 ◽  
Author(s):  
EJ Browne
Keyword(s):  
Magnesium Oxide ◽  
Cyanogen Bromide ◽  
Functional Group ◽  
Cyclic Ketones ◽  
Ring Systems ◽  
Derivatives Of ◽  
Medium Ring

Derivatives of two new diannulated azecine systems have been prepared by ring degradation of precursor bases with cyanogen -bromide-induced solvolysis. Reaction of a tetrahydro-5H-benzo[h] thieno [2,3,-a] quinolizine (5a) and a tetrahydro-7H-benzo[h][1] benzothieno [2,3-a] quinolizine (5b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded derivatives of a hexahydrobenzo [d] thieno [2,3-g] azecine (6a) and a hexahydrobenzo [d][1] benzothieno [2,3-g] azecine (6b), respectively. Functional group interconversions of these medium-ring systems were performed, including oxidations to cyclic ketones. The 5H-benzo[h] thieno [2,3-a] quinolizine and 7H-benzo[h] [l] benzothieno [2,3-a] quinolizine bases (5a) and (5b) are the first reported examples of these ring systems.

The Meisenheimer Rearrangement in Heterocyclic Synthesis. IV. Derivatives of the 2H,6H-1,5,4-Benzodioxazocine and 7H-1,6,5-Benzodioxazonine Ring Systems: X-Ray Crystal Structure of 10-Methoxy-5-methyl-7-phenyl-2,3,4,5-tetrahydro-7H-1,6,5-benzodioxazonine

1988 ◽  
Vol 41 (3) ◽  
pp. 293 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
LM Engelhardt ◽  
IWK Gunawardana ◽  
AH White
Keyword(s):  
Molecular Structure ◽  
Crystal Structure ◽  
Crystal And Molecular Structure ◽  
Ring System ◽  
Heterocyclic Synthesis ◽  
Rearrangement Product ◽  
Ring Systems ◽  
X Ray ◽  
Derivatives Of ◽  
Moderate Yield

Meisenheimer rearrangement of the N-oxides (4) derived from a series of 5-aryl-4-methyl-2,3,4,5-tetrahydro-1,4-benzoxazepines (3) gave rise to eight derivatives (5) of the new 2H,6H-1,5,4-benzodioxazocine ring system. Reaction of 9-methoxy-5-methyl-6-phenyl-3,4,5,6- tetrahydro-2H-1,5-benzoxazocine (6) with 3-chloroperoxybenzoic acid gave an unstable N-oxide (7). A Meisenheimer rearrangement product from (7), 10-methoxy-5-methyl-7-phenyl-2,3,4,5-tetrahydro-7 H-1,6,5- benzodioxazonine (8), the first example of this ring system, was isolated directly in moderate yield on oxidation of (6) with cooling. The crystal and molecular structure of (8) has been determined by X-ray crystallographic methods.

Synthesis of 1H-[1]Benzothieno[3,2-d]azonine and [1]Benzothieno[3,2-d]azecine Derivatives

1985 ◽  
Vol 38 (5) ◽  
pp. 765 ◽  
Author(s):  
EJ Browne
Keyword(s):  
Aqueous Medium ◽  
Magnesium Oxide ◽  
Cyanogen Bromide ◽  
Functional Group ◽  
Ring System ◽  
Cyclic Ketones ◽  
Phenyl Derivative ◽  
E And Z Isomers ◽  
Derivatives Of ◽  
Medium Ring

Derivatives of two new [1] benzothieno medium-ring heterocyclic systems have been prepared by ring degradation using cyanogen bromide-induced solvolysis of tetracyclic precursors. Reaction of a hexahydro -[1] benzothieno [3,2-g] indolizine (4a) and a hexahydro-2H-[1] benzo-thieno [2,3-a] quinolizine (4b) with cyanogen bromide and magnesium oxide under solvolytic conditions yielded the hexahydro-1H-[1] benzothieno [3,2-d] azonines (5a) and (6a) and the octahydro -[1] benzothieno [3,2-d] azecines (5b) and (6b), respectively. Functional group interconversions of these medium-ring systems are described, including oxidations to the cyclic ketones (7) and (9). The 11b-phenyl derivative (13) of (4a) reacted under similar conditions to give both solvolysis (14) and (16) and elimination (15) medium-ring products, the ratios depending on the solvent. By contrast the analogous 9a-phenylthienoindolizine derivative (17) under these conditions gave only the medium-ring elimination product (18) in aqueous medium, and only the equivalent solvolysis product in methanol. Both the thieno and [1] benzothienoazonine elimination products (18) and (15) appear to be mixtures of E and Z isomers. The [1] benzothieno [3,2-g] indolizine bases (4a) and (13) are the first reported examples of this ring system.

Synthesis of Thieno[2,3-g][1,4]oxazonine and Thieno[2,3-h][1,5]oxazecine derivatives by cyanogen-bromide-induced ring expansion

1984 ◽  
Vol 37 (5) ◽  
pp. 1043 ◽  
Author(s):  
JB Bremner ◽  
EJ Browne ◽  
V Chohan ◽  
BF Yates
Keyword(s):  
Cyanogen Bromide ◽  
Ring Expansion ◽  
Standard Methods ◽  
Methyl Derivatives ◽  
Derivatives Of ◽  
Medium Ring

4-Phenyl-4,6,7,8,9,10-hexahydrothieno[2,3-g][1,4]oxazonine-8-carbonitrile (5a) and the analogous 4-phenyl-6,7,8,9,10,11-hexahydro-4H-thieno[2,3-h][1,5]oxazecine-9-carbonitrile (5b) were preparedin moderate yields by cyanogen bromide-induced ring expansion of the appropriate ω-(tetrahydrothieno[3,2-c]pyridyl)alkan-1-ol precursors (3). N-Methyl derivatives of these new fused medium-ring heterocyclic systems were prepared by standard methods.

scholarly journals Antimonial analogues of the acridine series. Dilhydrostibacridines

1933 ◽  
Vol 143 (848) ◽  
pp. 38-47 ◽  
Keyword(s):  
Nitro Derivative ◽  
Starting Material ◽  
Arsenic Compounds ◽  
Ring Systems ◽  
Nitrogen Ring ◽  
Derivatives Of

In pursuing our investigation out the antimony analogues of certain nitrogen ring-systems, we Lave now succeeded in obtaining derivatives of dilhydrostibacridines, of when some of the corresponding arsenic compounds have been studied recently by Gump and Stolzenburg. The starting material for the work was o -aminodiphenylmethane obtained from the corresponding nitro derivative when, in turn, was prepared from o -nitrobenzyl chloride and benzene by Taneseseu's modification of the Friedel-Crafts reaction.

Circular dichroism of benzylidene derivatives of glycerol and mannitol

1977 ◽  
Vol 30 (11) ◽  
pp. 2465 ◽  
Author(s):  
RM Carman ◽  
CJ Hawkins ◽  
JJ Kibby
Keyword(s):  
Circular Dichroism ◽  
Ring Systems ◽  
Cotton Effects ◽  
Derivatives Of ◽  
Circular Dichroïsm

The c.d. spectra are reported for a series of benzylidene derivatives of glycerol and mannitol containing 1,3-dioxolan, 1,3-dioxan and 1,3- dioxepan ring systems. The signs of the Cotton effects of 1Lb and 1La transitions of the phenyl chromophore have been rationalized in terms of recently proposed sector rules for these transitions.

ChemInform Abstract: CONDENSED THIOPHEN RING SYSTEMS PART 16, DERIVATIVES OF 11H-(1)BENZOTHIENO(2,3-B)(1)BENZOTHIOPYRAN

1975 ◽  
Vol 6 (5) ◽  
pp. no-no
Author(s):  
BRIAN IDDON ◽  
HANS SUSCHITZKY ◽  
DAVID S. TAYLOR ◽  
KEVAN E. CHIPPENDALE
Keyword(s):  
Ring Systems ◽  
Derivatives Of
Sign in / Sign up

Export Citation Format

Share Document