Molecules p. 15797 - 15806 (2015)
Update date:2022-08-16
Topics:
Manansala, Camille
Tranmer, Geoffrey K.
A series of simple 2-methylpyridines were synthesized in an expedited and convenient manner using a simplified bench-top continuous flow setup. The reactions proceeded with a high degree of selectivity, producing α-methylated pyridines in a much greener fashion than is possible using conventional batch reaction protocols. Eight 2-methylated pyridines were produced by progressing starting material through a column packed with Raney nickel using a low boiling point alcohol (1-propanol) at high temperature. Simple collection and removal of the solvent gave products in very good yields that were suitable for further use without additional work-up or purification. Overall, this continuous flow method represents a synthetically useful protocol that is superior to batch processes in terms of shorter reaction times, increased safety, avoidance of work-up procedures, and reduced waste. A brief discussion of the possible mechanism(s) of the reaction is also presented which involves heterogeneous catalysis and/or a Ladenberg rearrangement, with the proposed methyl source as C1 of the primary alcohol.
View MoreChengdu Baishixing Science and Technology Industry Co., Ltd.
website:http://www.cd-bsx.com
Contact:+86-28-88531548
Address:#217,North of Industry Road,Heshan Town,Pujiang County,Chengdu,Sichuan,China.
MedicalChem(Yancheng)Manuf.Co.,Ltd.
Contact:+86-515-84383366
Address:Touzeng BinHai, YanCheng City, JiangSu Province, China
Beijing Tianjia Chemical Science & Technology Co.,Ltd
Contact:86-0550-2392698
Address:No.388, Shiliang Road (East),
NINGXIA DARONG CHEMICALS & METALLURGY CO.,LTD.
Contact:86-952-2179751
Address:Darong Road, Dawukou, Shizuishan, Ningxia 753001, China
JiangXi Keyuan Biopharma Co., LTD.
Contact:+86-563-6833666
Address:Guangde Fine Chemical Zone, Anhui Province, China
Doi:10.1021/jo026718+
(2003)Doi:10.1021/acs.oprd.5b00294
(2015)Doi:10.1515/chempap-2015-0036
(2015)Doi:10.1021/acs.inorgchem.6b02270
(2017)Doi:10.1021/ol502207z
(2014)Doi:10.1002/asia.201801529
(2019)