14759-45-6Relevant academic research and scientific papers
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji,Terao, Nodoka,Niwa, Takashi,Hosoya, Takamitsu
, p. 11822 - 11834 (2021/07/31)
To enhance the practicality of photouncaging system using 3-acyl-2-methoxyindolizines, direct acylation of indolizines with carboxylic acids was developed using condensation reagents, generally used for peptide coupling. This method allowed for caging a broad range of carboxylic acids with indolizines. The method enabled a facile synthesis of water-soluble caged bioactive carboxylic acids having an intramolecular photosensitizer. The efficient release of carboxylic acids from the synthesized caged compounds upon red light irradiation was confirmed in neutral buffered solutions.
Copper acetate monohydrate: A cheap but efficient oxidant for synthesizing multi-substituted indolizines from pyridinium ylides and electron deficient alkenes
Hu, Huayou,Feng, Junjun,Zhu, Yulan,Gu, Ning,Kan, Yuhe
, p. 8637 - 8644 (2015/02/19)
We report a highly practical one-pot method for synthesizing multi-substituted indolizines from ?±-halide carbonyl compounds, pyridines and electron deficient alkenes in the presence of copper acetate monohydrate and sodium acetate in DMF. A variety of function groups are tolerable in standard reaction conditions, including aldehyde. 36 examples were presented. The yield of indolizine was from moderate to high. Furthermore, multi-substituted indolizines can be prepared at gram scale by this method.
New route synthesis of indolizines via 1,3-dipolar cycloaddition of pyridiniums and alkynes
Shang, Yongjia,Zhang, Min,Yu, Shuyan,Ju, Kai,Wang, Cuie,He, Xinwei
experimental part, p. 6981 - 6984 (2010/02/27)
A convenient synthesis of 2,3-di and 1,2,3-trisubstituted indolizines has been achieved via a 1,3-dipolar cycloaddition of pyridiniums and alkynes. Various alkynes and diynes were used instead of dimethyl acetylenedicarboxylate (DMAD) and its analogues in
The first approach to the synthesis of 1-unsubstituted 2- arylindolizines by intramolecular 1,5-dipolar cyclization of 2-(2- arylethenyl)pyridinium ylides in the presence of tetrakis(pyridine)cobalt (II) dichromate
Zhou, Jian,Yuefei, Hu,Hongwen, Hu
, p. 166 - 170 (2007/10/03)
The first approach to the preparation of 1-unsubstituted 2- arylindolizines by intramolecular 1,5-dipolar cyclization of 2-(2- arylethenyl)pyridinium ylides 2a-v in the presence of tetrakis(pyridine)cobalt (II) dichromate was developed. Several kinds of n
Indolizines 4. The synthesis of new 3-vinylindolizines.
Bue, G. De,Nasielski, J.
, p. 97 - 108 (2007/10/03)
New 3-vinylindolizines have been synthesized by two methods.The first strategy calls for the Wittig olefination of 3-acylindolizines with methylenetriphenylphosphorane or methoxymethylenetriphenylphosphorane.The best yields are obtained when the ylid is formed at room temperature and the condensation in refluxing THF.The required 3-acylindolizines were obtained by direct acylation of indolizines or by 1,3-dipolar cyclo-additions to acylmethylpyridinium ylids.The following 3-isopropenylindolizines were made with good yields: unsubstituted (18, 85percent), 2-methyl (10, 98percent), 2-C6H5 (17, 95percent), 1-COOMe (20, 98percent), 1-COOMe-2-C6H5 (22, 91 percent), 1,2-di-COOMe (24, 58percent).Also synthesized are the following 3-α-styrylindolizines: 2-C6H5 (19, 99percent), 1-COOMe (21, 93percent), 1-COOMe-2-C6H5 (23, 87percent), 1,2-diCOOMe (25, 66percent). 3-(α-Methyl-β-methoxyvinyl)indolizines E (26, 40percent) and Z (27, 40percent) were also obtained.The second strategy involves the 1,3-dipolar cyclo-addition of dipolarophiles to allylpyridinium ylids.The following new 3-vinylindolizines have been synthesized: 1-carbomethoxy-3-vinylindolizine (30, 21percent), 1,2-dicarbomethoxy-3-vinylindolizine (31, 16percent), 1-carbomethoxy-3-β-styrylindolizine (33, 43percent), 3-β-styrylindolizine (34, 17percent), 1-carbomethoxy-3-(β-carbomethoxy)vinylindolizine 38 (31percent).
Thermal Rearrangements of Cyclic Amine Ylides. VIII. Intramolecular Cyclization of 2-Ethynylpyridine N-Ylides into Indolizines and Cyclazines
Sashida, Haruki,Kato, Masanobu,Tsuchiya, Takashi
, p. 3826 - 3832 (2007/10/02)
Treatment of 6-unsubstituted 2-ethynyl-1-phenacylpyridinium bromides (10a-c) with 1,5-diazabicycloundec-5-ene in refluxing benzene resulted in cyclization to give the 3-benzoyl-indolizines (11) via the N-ylide intermediates 13, whereas heating the
