Synthetic Communications p. 1 - 12 (2020)
Update date:2022-08-11
Topics:
Berry, Shiwani
Bari, Shamsher S.
Yadav, Pooja
Garg, Ankita
Khullar, Sadhika
Mandal, Sanjay K.
Bhalla, Aman
An efficient protocol for the stereoselective synthesis of pyrazolo[5,1-b]thiazole-3-carboxylate tethered β-lactam conjugates 8a–j from novel pyrazolo [5,1-b]thiazole-3-carboxylate substituted Schiff’s bases 6a–f is reported here. The reaction between various ketene precursors and novel Schiff’s bases 6a–f afforded exclusive formation of trans-β-lactams 8a–j. The substrate scope of this approach was investigated extensively by varying different groups (R, Z). All the novel compounds were characterized using various spectroscopic techniques, such as FT-IR, 1H NMR, 13C NMR, elemental analysis, 13C NMR (DEPT-135), and mass spectrometry in representative cases. Single crystal X-ray crystallographic study of trans-ethyl 7-(1-(4-methoxyphenyl)-4-oxo-3-phenoxyazetidin-2-yl)-6-methyl-2-(methylthio)pyrazolo[5,1-b]thiazole-3-carboxylate 8a has confirmed the molecular structure and the stereochemical outcome. To the best of our knowledge, the synthesis of such types of Schiff’s bases and β-lactam conjugates has not been reported so far.
View MoreShanghai Yolne Chemical Co., Ltd
Contact:+86-21-62960152,61525205,61538832,61538837
Address:Floor 4,building 2, No. 3377, Kangxi Road, Pudong New District, Shanghai, China
ShangHai Original Economy-Trade Develop Co.,Ltd.,
Contact:86-21-68552131
Address:shanghai
Jiangxi Hessence Chemicals Co., Ltd.
Contact:+86 796 3511924
Address:Chengxi Industrial Park, Jishui County, Jiangxi Province 331600 China.
Shouguang Haogang Chemical Co., Ltd.
Contact:86-0536-5672678
Address:Bohai Chemical Industrial Park,
SHENZHEN PENGCHENG REDSTAR INDUSTRY CO.,LTD
Contact:+86-755-82412922
Address:Room 8066, East Block, Square City, Jiabin Road, Luohu District
Doi:10.1039/c9nj01192g
(2019)Doi:10.1002/ejic.201900169
(2019)Doi:10.1021/ol8012638
(2008)Doi:10.1039/c4nj00545g
(2014)Doi:10.1021/acscatal.1c00971
(2021)Doi:10.1002/ardp.19723050109
(1972)