Heterocyclization of Enediynes Promoted by Sodium Azide: A Case of Ambiguity of X-ray Data and Structure Revision

被引：23

作者：

Gulevskaya, Anna V. ^{[1
]}

Tyaglivy, Alexander S. ^{[1
]}

Pozharskii, Alexander F. ^{[1
]}

Nelina-Nemtseva, Julia I. ^{[1
]}

Steglenko, Dmitry V. ^{[1
]}

机构：

[1] Southern Fed Univ, Dept Organ Chem, Rostov Na Donu 344090, Russia

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 06期

基金：

俄罗斯基础研究基金会;

关键词：

ANIONIC CYCLOAROMATIZATION; NUCLEOPHILIC CYCLIZATIONS; METHOXIDE ADDITION; REACTIVITY; CHEMISTRY; ACIDS; 2,3-DIALKYNYLQUINOXALINES; 1,2-DIALKYNYLBENZENES; BENZOFULVENES; SELECTIVITY;

D O I：

10.1021/ol500125j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been shown that contrary to the literature data the tandem cyclization of (Z)-1-aryl-3-hexen-1,5-diynes promoted by sodium azide results in the formation of the corresponding [1,2,3]triazolo[1,5-a]pyridines, not 1H-benzotriazole derivatives. Apparently, incorrect structure elucidation made by previous investigators originates from misinterpretation of X-ray data. A number of new transformations of this type as well as X-ray and NMR experiments are discussed.

引用

页码：1582 / 1585

页数：4

共 42 条

[1] Chelation-controlled Bergman cyclization: Synthesis and reactivity of enediynyl ligands [J].

Basak, A ;

Mandal, S ;

Bag, SS .

CHEMICAL REVIEWS, 2003, 103 (10) :4077-4094

[2]

Bischoff L, 2008, COMPREHENSIVE HETERO, V11, P609

[3] Hybrids of amino acids and acetylenic DNA-photocleavers: optimising efficiency and selectivity for cancer phototherapy [J].

Breiner, Boris ;

Kaya, Kemal ;

Roy, Saumya ;

Yang, Wang-Yong ;

Alabugin, Igor V. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (20) :3974-3987

[4] Polyaromatic Ribbons from Oligo-Alkynes via Selective Radical Cascade: Stitching Aromatic Rings with Polyacetylene Bridges [J].

Byers, Philip M. ;

Alabugin, Igor V. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (23) :9609-9614

[5] Indeno[1,2-b]fluorenes: Fully Conjugated Antiaromatic Analogues of Acenes [J].

Chase, Daniel T. ;

Rose, Bradley D. ;

McClintock, Sean P. ;

Zakharov, Lev N. ;

Haley, Michael M. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (05) :1127-1130

[6] Reaction of (Z)-1-aryl-3-hexen-1,5-diynes with sodium azide:: Synthesis of 1-aryl-1H-benzotriazoles [J].

Chen, ZY ;

Wu, MJ .

ORGANIC LETTERS, 2005, 7 (03) :475-477

[7] Cyclizations of Alkynes: Revisiting Baldwin's Rules for Ring Closure [J].

Gilmore, Kerry ;

Alabugin, Igor V. .

CHEMICAL REVIEWS, 2011, 111 (11) :6513-6556

[8] Cyclizations of enediynes under the action of electrophiles [J].

Gulevskaya, A. V. ;

Lazarevich, R. Yu. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (01) :116-139

[9] Nucleophilic cyclizations of enediynes as a method for polynuclear heterocycle synthesis [J].

Gulevskaya, A. V. ;

Tyaglivy, A. S. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (01) :82-94

[10] A novel tandem cyclization of condensed 2,3-dialkynylpyrazines into [1,2,3]triazolo[1′,5′;1,2]pyrido[3,4-b]pyrazines promoted by sodium azide [J].

Gulevskaya, A. V. ;

Van Dang, Shee ;

Tyaglivy, A. S. ;

Pozharskii, A. F. ;

Kazheva, O. N. ;

Chekhlov, A. N. ;

Dyachenko, O. A. .

TETRAHEDRON, 2010, 66 (01) :146-151

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