Tandem [5+1]/[8+2] cycloaddition reactions involving phosphiranes and tropones: facile access to 6,5,7-fused tricyclic skeletons

被引：8

作者：

Cui, Mingyue ^{[1
]}

Li, Juan ^{[1
]}

Tian, Rongqiang ^{[1
]}

Duan, Zheng ^{[1
]}

机构：

[1] Zhengzhou Univ, Coll Chem, Green Catalysis Ctr, Int Phosphorus Lab,Int Joint Res Lab Funct Organo, 100 Sci Ave, Zhengzhou 450001, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 10期

基金：

中国国家自然科学基金;

关键词：

AZOMETHINE YLIDES; 8+2 ANNULATION; CHEMISTRY; COMPLEXES; CYCLOHEPTATRIENE; PERISELECTIVITY; CONSTRUCTION; PHOSPHORUS; MECHANISMS; AZIRIDINES;

D O I：

10.1039/d2qo00386d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem [5 + 1] carbonyl cyclization/[8 + 2] cycloaddition reactions of tropones and phosphiranes were developed as a straightforward synthetic method to synthesize structurally complex 6,5,7-fused tricyclic scaffolds. This one-pot reaction has excellent regio- and periselectivity. The P-O bond was formed exclusively. The highly reactive C=P bond enabled the high-order [8 + 2] cycloaddition of tropones.

引用

页码：2753 / 2758

页数：6

共 13 条

[1] Tandem [8+2] Cycloaddition-[2+6+2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines
Aginagalde, Maialen
Vara, Yosu
Arrieta, Ana
Zangi, Ronen
Cebolla, Vicente L.
Delgado-Camon, Arantzazu
Cossio, Fernando P.
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (09): : 2776 - 2784
[2] Rh(I)-Catalyzed Formal [5+1]/[2+2+1] Cycloaddition of 1-Yne-vinylcyclopropanes and Two CO Units: One-Step Construction of Multifunctional Angular Tricyclic 5/5/6 Compounds
Lin, Mu
Li, Feng
Jiao, Lei
Yu, Zhi-Xiang
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (06) : 1690 - 1693
[3] Syntheses of 6-8-5 tricyclic ring systems by carbonylative [2+2+1] cycloaddition of bis(allene)s
Shafawati, M. T. Soraya
Inagaki, Fuyuhiko
Kawamura, Takamasa
Mukai, Chisato
TETRAHEDRON, 2013, 69 (05) : 1509 - 1515
[4] A new Co2(CO)8-mediated tandem [5+1]/[2+2+l]-cycloaddition reaction:: A one-pot synthesis of tricyclic δ-lactones from cis-epoxy ene-ynes
Odedra, A
Wu, CJ
Madhushaw, RJ
Wang, SL
Liu, RS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) : 9610 - 9611
[5] A new Co2(CO)8-mediated tandem [5 + 1]/[2 + 2 + 1]-cycloaddition reaction: A one-pot synthesis of tricyclic δ-lactones from cis-epoxy ene-ynes
1600, American Chemical Society (125):
[6] [4 + 2] Cycloaddition reactions involving 1,3-diphosphacyclopentadiene and 1,2,4-triphosphacyclopentadiene: crystal and molecular structures of the exo-compounds and P5C5 tBu5H2 P4C6tBu6H2
Caliman, V.
Hitchcock, P. B.
Nixon, J. F.
Journal of Organometallic Chemistry, 536/5 (1-2):
[7] Substituted, Fused, Tricyclic 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-3-amines by Isocyanide-Abetted Cycloaddition Reaction
Azad, Chandra S.
Narula, Anudeep K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (43) : 6413 - 6416
[8] [4+2] cycloaddition reactions involving 1,3-diphosphacyclopentadiene and 1,2,4-triphosphacyclopentadiene: Crystal and molecular structures of the exo-compounds P5C5(t)Bu5H2 and P4C6(t)Bu6H2
Caliman, V
Hitchcock, PB
Nixon, JF
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 536 (1-2) : 273 - 279
[9] Synthesis of Multifunctionalized 1,2,3,4-Tetrahydropyridines, 2,3-Dihydropyridin-4(1H)-ones, and Pyridines from Tandem Reactions Initiated by [5+1] Cycloaddition of N-Formylmethyl-Substituted Enamides to Isocyanides: Mechanistic Insight and Synthetic Application
Lei, Chuan-Hu
Wang, De-Xian
Zhao, Liang
Zhu, Jieping
Wang, Mei-Xiang
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (50) : 16981 - 16987
[10] STUDIES ON FUSED PYRIMIDINE DERIVATIVES .11. A FACILE GENERATION AND STEREOSELECTIVE CYCLOADDITION REACTIONS OF 5,6-DIHYDRO-5,6-BIS(METHYLENE)-2,4(1H,3H)-PYRIMIDINEDIONE INTERMEDIATE
YASUE, N
ISHIKAWA, S
NOGUCHI, M
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (10) : 2845 - 2847

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