![Ethyl 3-((6-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2-(pyridin-2-yl)pyrimidin-4-yl)amino)propanoate structure](https://static.chemtradehub.com/structs/137/1373423-53-0-496a.webp "Ethyl 3-((6-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2-(pyridin-2-yl)pyrimidin-4-yl)amino)propanoate structure")
Ethyl 3-((6-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-2-(pyridin-2-yl)pyrimidin-4-yl)amino)propanoate
CAS Number:
1373423-53-0
Molecular Formula:
C24H27N5O2
Highly regioselective, electrophile induced cyclizations of 2-(prop-1-ynyl)benzamides
Literature Information
Publication Date
2018-04-26
DOI
10.1039/C8OB00434J
Impact Factor
3.876
Authors
Bhavani Shankar Chinta, Harikrishna Sanapa, Kamala Prasad Vasikarla, Beeraiah Baire
View Original
Abstract
We report an electrophile promoted, highly regioselective (∼100%) synthesis of 5-membered haloimidiates from 2-(1-alkynyl)benzamides under metal free conditions. The steric bulk in association with neighbouring group assistance at the propargylic carbon of an alkyne has been employed as the dictating factor to achieve the regioselectivity. A very broad structural diversity has been observed for propargylic alcohols and acetates, and for amide functional groups. Control experiments supported the role of the steric bulk as well as neighbouring group assistance from the oxygen atom of the substituent for the observed high regioselectivity.
Recommended Journals
Related Literature
Scalable electrochemical oxidant-and metal-free dehydrogenative coupling of S–H/N–H
Shanyu Tang, Yan Liu, Longjia Li, Xuanhe Ren, Jiao Li, Guanyu Yang, Heng Li, Bingxin Yuan
2019-01-10
Communication
DOI: 10.1039/C8OB03211D
Iodine-promoted radical alkyl sulfuration of imidazopyridines with dialkyl azo compounds and elemental sulfur
Yong-Chao Gao, Zhuo-Bin Huang, Li Xu, Zhao-Dong Li, Zhi-Sheng Lai
2019-02-01
Paper
DOI: 10.1039/C8OB03191F
Expeditious access of chromone analogues via a Michael addition-driven multicomponent reaction
Liu-Jun He, Ya-Fei Luo, Dian-Yong Tang, Wei Yan, Hui-Kuan Lin, Hong-yu Li, Zhong-Zhu Chen, Zhi-Gang Xu
2020-03-06
Research Article
DOI: 10.1039/D0QO00145G
Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent
Karen de la Vega-Hernández, Raffaele Senatore, Margherita Miele, Ernst Urban, Wolfgang Holzer, Vittorio Pace
2018-10-22
Paper
DOI: 10.1039/C8OB02312C
Hydroaminoalkylation of sterically hindered alkenes with N,N-dimethyl anilines using a scandium catalyst
Jianhong Su, Yiqun Zhou, Xin Xu
2018-12-10
Paper
DOI: 10.1039/C8OB02657B
Metal-free chemoselective hydrogenation of unsaturated carbon–carbon bonds via cathodic reduction
Yongwei Qin, Jingjun Lu, Zirong Zou, Huanliang Hong, Yamei Li, Yibiao Li, Lu Chen, Jinhui Hu, Yubing Huang
2020-06-04
Research Article
DOI: 10.1039/D0QO00547A
Diastereoselective synthesis of 3,3-disubstituted 3-nitro-4-chromanone derivatives as potential antitumor agents
Huiqing Chen, Jia Xie, Dong Xing, Jinping Wang, Jie Tang, Zhengfang Yi, Fei Xia, Wen-Wei Qiu, Fan Yang
2019-01-07
Communication
DOI: 10.1039/C8OB02761G
Tricarabrols A–C, three anti-inflammatory sesquiterpene lactone trimers featuring a methylene-tethered linkage from Carpesium faberi
Xuelan Wen, Chang-Qiang Ke, Tian Zhang, Ligen Lin, Sheng Yao, Jason D. Goodpaster, Chunping Tang
2020-04-22
Research Article
DOI: 10.1039/D0QO00093K
Direct (het)arylation of tetrahydroisoquinolines via a metal and oxidant free C(sp3)–H functionalization enabled three component reaction
Surajit Haldar, Chandan K. Jana
2018-11-26
Communication
DOI: 10.1039/C8OB02309C
You might also like
Compound Q&A
What industries use (1R,3S)-1,3-Cyclopentanediol (CAS: 16326-97-9)?
(1R,3S)-1,3-Cyclopentanediol finds applications in various industries. In the ph...
16326-97-9(1R,3S)-1,3-Cyclopen...
Compound Q&A
What precautions should be taken when handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine (CAS: 637-31-0)?
When handling N'-[4-(Dimethylamino)phenyl]-N,N-dimethyl-1,4-benzenediamine, it i...
637-31-0N'-[4-(Dimethylamino...
Compound Q&A
Are there alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine (CAS: 1352318-16-1) in synthesis?
There are several alternatives to 5-(2,4-Difluorophenyl)-2-methoxypyrimidine in ...
1352318-16-15-(2,4-Difluoropheny...
Compound Q&A
What regulatory guidelines apply to 1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6)?
1-(3-Methoxyphenoxy)propan-2-ol (CAS: 382141-68-6) must comply with the Globally...
382141-68-61-(3-Methoxyphenoxy)...
Compound Q&A
Is Tetrodotoxin Citrate (CAS: 18660-81-6) safe?
Tetrodotoxin Citrate is extremely dangerous and should be handled with extreme c...
18660-81-6Tetrodotoxin Citrate
Compound Q&A
What are the main uses of 2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9)?
2-Methyl-2-propanyl [(1R,3S)-3-hydroxycyclopentyl]carbamate (CAS: 225641-84-9) i...
225641-84-92-Methyl-2-propanyl ...
Compound Q&A
How should waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) be handled?
Waste containing 4-(2-Hydroxyhexafluoroisopropyl)Benzoic Acid (CAS: 16261-80-6) ...
16261-80-64-(2-Hydroxyhexafluo...
Compound Q&A
How is 2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl}carbamate (CAS: 102507-19-7) typically synthesized?
2-Methyl-2-proanyl {(2S)-1-[(benzyloxy)amino]-3-hydroxy-3-methyl-1-oxo-2-butanyl...
102507-19-72-Methyl-2-propanyl ...
Compound Q&A
What is Benzeneethanamine, α-ethyl-, hydrochloride (1:1) (CAS: 20735-15-3)?
Benzeneethanamine, α-ethyl-, hydrochloride (1:1) is an organic compound with the...
20735-15-3Benzeneethanamine, α...
Compound Q&A
Are there alternatives to 3-{(E)-[4-(Dimethylamino)phenyl]diazenyl}benzoic acid (CAS: 20691-84-3) in synthesis?
In the synthesis of compounds similar to 3-{(E)-[4-(Dimethylamino)phenyl]diazeny...
20691-84-33-{(E)-[4-(Dimethyla...
Source Journal
Organic & Biomolecular Chemistry
CiteScore:
3.4
Self-citation Rate:
10.3%
Articles per Year:
1041
Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.
Recommended Compounds
Recommended Suppliers
Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.