Heteroarene-tethered Functionalized Alkyne Metamorphosis

被引:22
作者
Bag, Debojyoti [1 ]
Sawant, Sanghapal D. [1 ]
机构
[1] CSIR Indian Inst Integrat Med, Lab 212, Div Med Chem, Jammu 180001, Jammu & Kashmir, India
关键词
alkynes; cycloisomerization; functionalization; heteroarene; metamorphosis; GOLD-CATALYZED SYNTHESIS; UGI INTRAMOLECULAR HYDROARYLATION; GARRATT-BRAVERMAN CYCLIZATION; CONTAINING NATURAL-PRODUCTS; ASYMMETRIC TOTAL-SYNTHESIS; VERSATILE BUILDING-BLOCKS; PROMOTED TANDEM REACTION; FORMAL TOTAL-SYNTHESIS; DIELS-ALDER REACTION; CARBON SIGMA-BONDS;
D O I
10.1002/chem.202002154
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Heteroarene-tethered functionalized alkynes are multipotent synthons in organic chemistry. This detailed Review described herein offers a thorough discussion of the metamorphosis of heteroarene-tethered functionalized alkynes, an area which has earned much attention over the past decade in the straightforward synthesis of architecturally complex heterocyclic scaffolds in atom and step economic manner. Depending upon the variety of functionalized alkynes, this Review is divided into multiple sections. Amongst the vast array of synthetic transformations covered, dearomatizing spirocyclizations and cascade spirocyclization/rearrangement are of great interest. Synthetic transformations involving the heteroarene-tethered functionalized alkynes with scope, challenges, limitations, mechanism, their application in the total synthesis of natural products and future perceptions are surveyed.
引用
收藏
页码:1165 / 1218
页数:54
相关论文
共 317 条
[1]   Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles [J].
Abbiati, Giorgio ;
Arcadi, Antonio ;
Marinelli, Fabio ;
Rossi, Elisabetta .
SYNTHESIS-STUTTGART, 2014, 46 (06) :687-721
[2]   Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals [J].
Abu Sohel, Shariar Md. ;
Liu, Rai-Shung .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2269-2281
[3]   Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].
Ackermann, Lutz .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295
[4]   Recent Advances in Catalytic Transformations Involving Copper Acetylides [J].
Adeleke, A. Francis ;
Brown, Alexander P. N. ;
Cheng, Li-Jie ;
Mosleh, Kari A. M. ;
Cordier, Christopher J. .
SYNTHESIS-STUTTGART, 2017, 49 (04) :790-801
[5]   1,3-Dien-5-ynes: Versatile Building Blocks for the Synthesis of Carbo- and Heterocycles [J].
Aguilar, Enrique ;
Sanz, Roberto ;
Fernandez-Rodriguez, Manuel A. ;
Garcia-Garcia, Patricia .
CHEMICAL REVIEWS, 2016, 116 (14) :8256-8311
[6]  
Ahlsten N., 2016, AU CATALYZED SYNTHES, P175, DOI DOI 10.1007/7081_2015_5005
[7]   Synthesis of quinoxalines or quinolin-8-amines from N-propargyl aniline derivatives employing tin and indium chlorides [J].
Aichhorn, Stefan ;
Himmelsbach, Markus ;
Schoefberger, Wolfgang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (36) :9373-9380
[8]   Regiodivergent Trifluoromethanesulfonic Acid-Promoted Cycloisomerizations of Ynenamines to Fused Indoles [J].
Alam, Khyarul ;
Kim, Jin Gyeong ;
Kang, Dong Yun ;
Park, Jin Kyoon .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (07) :1683-1688
[9]   A Facile Synthesis of Blue Luminescent [7]Helicenocarbazoles Based on Gold-Catalyzed Rearrangement-Iodonium Migration and Suzuki-Miyaura Benzannulation Reactions [J].
Alcaide, Benito ;
Almendros, Pedro ;
Aragoncillo, Cristina ;
Busto, Eduardo ;
Lopez-Calixto, Carmen G. ;
Liras, Marta ;
de la Pena O'Shea, Victor A. ;
Garcia-Sanchez, Alba ;
Stone, Hannah V. .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (30) :7620-7625
[10]   Versatile Synthesis of Polyfunctionalized Carbazoles from (3-Iodoindol-2-yl)butynols via a Gold-Catalyzed Intramolecular Iodine-Transfer Reaction [J].
Alcaide, Benito ;
Almendros, Pedro ;
Alonso, Jose M. ;
Busto, Eduardo ;
Fernandez, Israel ;
Pilar Ruiz, M. ;
Xiaokaiti, Gulinigaer .
ACS CATALYSIS, 2015, 5 (06) :3417-3421