- Application of primary halogenated hydrocarbons for the synthesis of 3-Aryl and 3-Alkyl indolizines
-
Indolizine is an important heterocyclic compound with several interesting properties that make it suitable for numerous applications in many fields, such as biology, medicine and materials. However, the synthesis of 3-Alkyl indolizines from bulky primary halogenated alkanes has not yet been reported. Herein, a transition-metal-free synthetic route to 3-Aryl and 3-Alkyl indolizines from electron-deficient alkenes, pyridines and primary halogenated hydrocarbons has been reported for the first time using a tandem reaction. The key step of this method is the oxidative dehydrogenative aromatization of a tetrahydroindolizine intermediate with 2,2,6,6-Tetramethylpiperidine-N-oxyl (TEMPO) as the oxidant. The advantages of this protocol are its use of easily available and low-cost starting materials, the transition-metal-free conditions and its ready scalability.
- Liu, Yan,Hu, Huayou,Zhou, Junyu,Wang, Wenhui,He, Youliang,Wang, Chao
-
p. 5016 - 5024
(2017/07/10)
-
- Synthesis of novel tetrahydrobenzazepine derivatives and their cytoprotective effect on human lymphocytes
-
Cytoprotective compounds such as amifostine play an important role in chemo- and radiotherapy due to their ability to reduce the side effects of these treatments. Our work was initiated with the intention to design, synthesise and test a new class of hete
- Simic, Milena R.,Stankovic, Miroslava,Mandic, Boris M.,Tesevic, Vele V.,Savic, Vladimir M.
-
p. 100 - 112
(2015/02/19)
-
- A one-pot domino reaction for the synthesis of 3-arylindolizines from pyridines, benzyl halides, and dihalide-substituted electron-deficient alkenes
-
3-Arylindolizines were prepared by one-pot domino reactions from benzyl halides with pyridine (or isoquinoline) and cyclic or acyclic dihalide-substituted electron-deficient alkenes in the presence of potassium carbonate via in situ generated N-ylide intermediate. Both electron-donating and electron-withdrawing groups are tolerated in the aryl ring of benzyl halides. The yields range from moderate to high. Georg Thieme Verlag Stuttgart - New York.
- Hu, Huayou,Shi, Kunbo,Hou, Rongrong,Zhang, Zaichao,Zhu, Yulan,Zhou, Jianfeng
-
experimental part
p. 4007 - 4014
(2011/02/22)
-
- Orientation and alkylation effects on cation-π interactions in aqueous solution
-
We have investigated the orientation dependence of the cation-π interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol-1, with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.
- Rashkin, Mark J.,Hughes, Robert M.,Calloway, Nathaniel T.,Waters, Marcey L.
-
p. 13320 - 13325
(2007/10/03)
-
- Intramolecular Photocyclization of N-pyridinium and N-(Arylmethyl)-2-halopyridinium Salts
-
Various N-pyridinium, N-(arylmethyl)-2-halopyridinium and N-(2-halobenzyl)isoquinolinium salts have been synthesized and their intramolecular photocyclization reactions studied.Upon irradiation the aqueous solution of N-(2-haloaryl)me
- Park, Y.-T.,Joo, C.-H.,Choi, C.-D.,Park, K.-S.
-
p. 1083 - 1089
(2007/10/02)
-