On the cyclization of ortho-alkynylbenzene diazonium salts

Fedenok, L. G.; Zolnikova, Nataliya A.

doi:10.1016/s0040-4039(03)01295-4

Cited by 25 publications

(10 citation statements)

References 6 publications

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“…Similarly, alkynyl Richter cyclizations onto aryl diazonium salts are assisted by external species . Interestingly, the regioselectivity for these latter closures can be controlled either with temperature or the nature of the preexisting cyclic core (Scheme ) …”

Section: Extension 4: Promoted Cyclizationsmentioning

confidence: 99%

The Baldwin rules: revised and extended

Gilmore

Mohamed

Alabugin

2016

WIREs Comput Mol Sci

136

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The Baldwin rules constitute one of the clearest examples of the success which can be obtained through the application of stereoelectronic concepts to reaction design. With thousands of examples, the predictive power of these rules is inarguable. However, time has revealed a number of exceptions and gray areas within these rules, leading to extensions and revisions. In this review, we will present an overview of how subsequent studies of ring closure have clashed with several of Baldwin's predictions, leading to the revision of some classes of ring closure (alkyne cyclizations, electrophilic closures, etc.). We also discuss for which the original rules were vague (epoxides) or absent (promoted cyclizations), and the evidence revealed since Baldwin's work that has allowed for a better understanding of these ambiguities. With the concise summation of these amendments, this review aims to present an overview of the understanding of cyclization reactions to date. For further resources related to this article, please visit the WIREs website

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Section: Extension 4: Promoted Cyclizationsmentioning

confidence: 99%

The Baldwin rules: revised and extended

Gilmore

Mohamed

Alabugin

2016

WIREs Comput Mol Sci

136

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“…Moreover, this approach permits us to probe the reasons which prevent the formation of the cyclization product from 2-(4-dimethylaminophenylethynyl)aniline. 9 The absence of cyclization product is ascribed not to the efficiency of the cyclization step as was suggested earlier? but rather to the diazotization step.…”

Section: Oppi Briefsmentioning

confidence: 79%

IMPROVED METHOD FOR THE CYCLIZATION OFortho-ALKYNYLBENZENEDIAZONIUM SALTS

Zolnikova¹,

Fedenok²,

Polyakov³

2006

Organic Preparations and Procedures International

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“…On the basis of quantum-chemical calculations of the energy profile of the reaction [80] it was concluded that the cyclization of the arenediazonium salt with the formation of both a six-membered ring and a five-membered ring is an energetically unfavorable process with a high activation energy. Moreover, attack by the terminal nitrogen atom at the β-carbon atom of the triple bond is unlikely on account of the large distance between them.…”

Section: + +mentioning

confidence: 99%

“…The same authors carried out investigations into the effect of the reaction conditions and the nature of the substituent at the triple bond for the Richter reaction in the series of ortho-phenylethynylanilines [80,81]. As in the case of naphthoquinones the cyclization was carried out in three versions: with dilution of the reaction mixture containing the diazonium salt with water and with concentrated solutions of NaCl and HCl.…”

Section: + +mentioning

confidence: 99%

Methods for the synthesis of cinnolines (review)

Vinogradova

Балова

2008

Chem Heterocycl Comp

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This review analyses the principal approaches to the synthesis of the cinnoline nucleus, used as synthetic precursors of arenediazonium salts, arylhydrazones, and arylhydrazines, and also reductive methods for the synthesis of polycondensed derivatives of cinnoline. The mechanisms of the transformations and the possibilities and limitations of the various methods are discussed. Special attention is paid to methods based on the cyclization of derivatives of arenediazonium salts, which have been developed substantially in recent years.

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On the cyclization of ortho-alkynylbenzene diazonium salts

Cited by 25 publications

References 6 publications

The Baldwin rules: revised and extended

The Baldwin rules: revised and extended

IMPROVED METHOD FOR THE CYCLIZATION OFortho-ALKYNYLBENZENEDIAZONIUM SALTS

Methods for the synthesis of cinnolines (review)

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