2010
DOI: 10.1248/cpb.58.685
|View full text |Cite
|
Sign up to set email alerts
|

Polycyclic N-Heterocyclic Compounds. Part 64: Synthesis of 5-Amino-1,2,6,7-tetrahydrobenzo[f]furo[2,3-c]isoquinolines and Related Compounds. Evaluation of Their Bronchodilator Activity and Effects on Lipoprotein Lipase mRNA Expression

Abstract: Regular ArticleThe Truce-Smiles rearrangement features an intramolecular aromatic substitution reaction by a C-nucleophile making it a particularly useful rearrangement reaction because of the formation of a new C-C bonds.2-6) Recently, we found that this rearrangement could be extended to aliphatic electrondeficient alkenes as well as aromatic substrates.7) Thus, treatment of 2-(3-cyanopropoxy)cyclohexene-1-carbonitrile (1) with base gives a modest yield (15-43%) of 5-amino-1, 2,6,7,8,9-hexahydrofuro[2,3-c]is… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1

Citation Types

0
9
0

Year Published

2010
2010
2017
2017

Publication Types

Select...
6
1

Relationship

2
5

Authors

Journals

citations
Cited by 12 publications
(9 citation statements)
references
References 18 publications
0
9
0
Order By: Relevance
“…mp 220-221°C. 1 In a similar procedure as described above for aniline, 4-chloroaniline (0.993 mmol scale at 80°C for 20 min) produced the same compound 7 (38%) identical with 7 formed from aniline.…”
Section: -Bromo-1-vinyl-56-dihydrobenzo[f]isoquinolin-2(3h)-one (7)mentioning
confidence: 94%
See 3 more Smart Citations
“…mp 220-221°C. 1 In a similar procedure as described above for aniline, 4-chloroaniline (0.993 mmol scale at 80°C for 20 min) produced the same compound 7 (38%) identical with 7 formed from aniline.…”
Section: -Bromo-1-vinyl-56-dihydrobenzo[f]isoquinolin-2(3h)-one (7)mentioning
confidence: 94%
“…The residue was chromatographed on silica gel and the eluate of benzene-ethyl acetate (4 : 1) was evaporated and the residue was recrystallized from methanol to give 10b (243 mg, 69%) as colorless prisms, mp 121-122°C. 1 (3H, 1H, 1H, 3H, each m, H-5, 6, 7, 1Ј), 3.39, 3.65 (each 2H, each …”
Section: -Bromo-1-(2-ethoxyethyl)-56-dihydrobenzo[f]isoquinolin-2(3mentioning
confidence: 99%
See 2 more Smart Citations
“…However, the reaction has recently begun to receive a more systematic investigation by researchers such as Takashi Hirota [18][19][20][21][22][23][24][25][26][27][28] and Timothy Snape. [29][30][31] Despite our awareness of the Truce-Smiles rearrangement for 60 years, there remain many unanswered questions about the scope and limitations of this reaction.…”
Section: Introductionmentioning
confidence: 99%