Polarized ethylene. V. Synthesis of 1-substituted indolizine, pyrazolo[1,5-a]pyridine, and their related compounds using methoxyethylene derivatives
TL;DR: The reaction of pyridinium or isoquinolinium N-ylides with methoxy-substituted ethylenes gave the corresponding indolizine and pyrrolo[2,1-a]isoquinoline derivatives bearing acetyl, aroyl, cyano, ester group at the 1-position in one step as mentioned in this paper.
About: This article is published in Journal of Heterocyclic Chemistry.The article was published on 1990-02-01. It has received 32 citations till now. The article focuses on the topics: Indolizine & Isoquinoline.
Citations
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TL;DR: Piperazinylmethyl substituted pyrazolo[1,5-a]pyridines and related heterocycles were synthesized and found to recognize selectively the dopamine D4 receptor and a Ki value of 2.0 nM was observed.
90 citations
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TL;DR: Rhodium(III)-catalyzed oxidative annulation reactions of pyridinium trifluoromethanesulfonate salts with alkynes leading to substituted indolizines by cleavage of C(sp(2)-H/C(3))-H bonds are developed and provide a new efficient route to indolIZine derivatives.
59 citations
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TL;DR: The indolizine core can be constructed from a pyridine, two aldehydes, and a nitroalkane, and no undesired functional groups remain in the products as discussed by the authors.
59 citations
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TL;DR: The Cu-catalyzed three-component reaction between quinolines, diazo compounds, and alkenes has been established for direct construction of indolizine derivatives via quinolinium ylides.
Abstract: The Cu-catalyzed three-component reaction between quinolines, diazo compounds, and alkenes has been established for direct construction of indolizine derivatives via quinolinium ylides. This methodology is distinguished by the use of a commercially inexpensive catalyst and readily available starting materials, wide substrate scope, and operational simplicity.
55 citations
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TL;DR: In this paper, a facile and general one-step method is presented for the synthesis of aromatic indolizine compounds 3a-n in moderate to high yields (53-99%) by reaction of the pyridinium N-ylides 1a, e, f, g, and isoquinolinium Nylide 1g with various olefinic dipolarophiles, such as acrylonitrile 2a, methyl acrylate 2b, acrylamide 2c, diethyl maleate 2d and methyl croton
Abstract: A facile and general one-step method is presented for the synthesis of aromatic indolizine compounds 3a–n in moderate to high yields (53–99%) by reaction of the pyridinium N-ylides 1a–e, the quinolinium N-ylide 1f and the isoquinolinium N-ylide 1g with various olefinic dipolarophiles, such as acrylonitrile 2a, methyl acrylate 2b, acrylamide 2c, diethyl maleate 2d and methyl crotonate 2e, respectively, in the presence of a new oxidant TPCD [Copy4(HCrO4)2, tetrapyridinecobalt(II) dichromate] at 90 °C for 2 h in DMF.
49 citations
References
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TL;DR: In this article, the LCAO MO treatment of the orientation problem in chemical reactions of π-electron systems is subjected to an extension in the sense that the frontier orbitals are specified according to the type of reaction.
Abstract: As to the LCAO MO treatment of the orientation problem in chemical reactions of π‐electron systems, the frontier electron concept which has been previously introduced by the authors for explaining the reactivities in aromatic hydrocarbons is subjected to an extension in the sense that the frontier orbitals are specified according to the type of reaction. Thus, fundamental postulates relating to the reactivities of π‐electron systems are set up, which are believed to include general principles involved in the mechanism of both substitution and addition of electrophilic, nucleophilic, or radical type. On the basis of these postulates it is possible to predict the position of attack in conjugated molecules in all the three types of substitution as well as addition in a consistent manner. There is a nearly perfect agreement between the theoretical conclusions and experimental results hitherto reported.
622 citations
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01 Jan 198437 citations
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TL;DR: The synthesis of indolizine derivatives and their related compounds using ketene dithioacetals is described in this paper, where the 1, 5-dipolar cyclization is used.
Abstract: The synthesis of indolizine derivatives and their related compounds using ketene dithioacetals is described. This review is concerned with following five items : 1) the 1, 5-dipolar cyclization ; 2) the reaction of picolinium salts with ketene dithioacetals ; 3) the reaction of 2-pyridyl ketene dithioacetals with α-halocarbonyl compounds ; 4) the reaction of pyridinium or isoquinolinium ketene dithioacetals ; 5) the reaction of N-imines or S-imine with ketene dithioacetals.
30 citations
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TL;DR: In this article, the reactivity of heteroaromatic N-imides and their dimers is discussed, and it is shown that the dimers behave as expected for aromatic azomethine imines as 1,3-dipoles.
25 citations