Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization
Shixian Deng
1, 2
,
Zhenzhuang Cheng
1
,
Charles Ingalls
1
,
Ferenc Kontes
1
,
JIAMING YAN
1
,
Sandro Belvedere
1
1
ARMGO Pharma, Inc., 777 Old Saw Mill River Road, Tarrytown, New York 10591, United States
|
Publication type: Journal Article
Publication date: 2017-10-09
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
We report an efficient and scalable synthesis of 7-methoxy-2,3,4,5-tetrahydrobenzo[1,4]thiazepine, the core structure of biologically active molecules like JTV-519 and S107. This synthetic route, starting with 4-methoxythiophenol and proceeding via acyliminum cyclization, gives the target product in four steps and 68% overall yield and is a substantial improvement over previously published processes. Nine additional examples of tetrahydrobenzo[1,4]thiazepine synthesis via acyliminium ring closure are also presented.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Journal of Organic Chemistry
2 publications, 40%
|
|
|
1
2
|
Publishers
|
1
2
|
|
|
American Chemical Society (ACS)
2 publications, 40%
|
|
|
Royal Society of Chemistry (RSC)
1 publication, 20%
|
|
|
1
2
|
- We do not take into account publications without a DOI.
- Statistics recalculated weekly.
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
5
Total citations:
5
Citations from 2024:
2
(40%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Deng S. et al. Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization // Organic Process Research and Development. 2017. Vol. 21. No. 11. pp. 1801-1805.
GOST all authors (up to 50)
Copy
Deng S., Cheng Z., Ingalls C., Kontes F., YAN J., Belvedere S. Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization // Organic Process Research and Development. 2017. Vol. 21. No. 11. pp. 1801-1805.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.oprd.7b00260
UR - https://doi.org/10.1021/acs.oprd.7b00260
TI - Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization
T2 - Organic Process Research and Development
AU - Deng, Shixian
AU - Cheng, Zhenzhuang
AU - Ingalls, Charles
AU - Kontes, Ferenc
AU - YAN, JIAMING
AU - Belvedere, Sandro
PY - 2017
DA - 2017/10/09
PB - American Chemical Society (ACS)
SP - 1801-1805
IS - 11
VL - 21
SN - 1083-6160
SN - 1520-586X
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2017_Deng,
author = {Shixian Deng and Zhenzhuang Cheng and Charles Ingalls and Ferenc Kontes and JIAMING YAN and Sandro Belvedere},
title = {Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization},
journal = {Organic Process Research and Development},
year = {2017},
volume = {21},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.oprd.7b00260},
number = {11},
pages = {1801--1805},
doi = {10.1021/acs.oprd.7b00260}
}
Cite this
MLA
Copy
Deng, Shixian, et al. “Synthesis of 2,3,4,5-Tetrahydrobenzo[1,4]thiazepines via N-Acyliminium Cyclization.” Organic Process Research and Development, vol. 21, no. 11, Oct. 2017, pp. 1801-1805. https://doi.org/10.1021/acs.oprd.7b00260.