First synthesis of both 1-aryl-4-[(E)-alk-1-enyl]-1H-1,2,3-triazoles and 1-aryl-4-[(Z)-1-(trimethylsilyl)alk-1-enyl]-1H-1,2,3-triazoles: assembly of π-extended 1,2,3-triazoles using a cross-coupling/click reaction sequence

Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor.

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Towards the Total Synthesis of Schisandrene: Stereoselective Synthesis of the Dibenzocyclooctadiene Lignan Core

Synlett ◽

10.1055/s-0036-1591539 ◽

2018 ◽

Vol 29 (07) ◽

pp. 908-911 ◽

Cited By ~ 2

Author(s):

K. Babu ◽

Arramshetti Venkanna ◽

Borra Poornima ◽

Bandi Siva ◽

B. Babu

Keyword(s):

Total Synthesis ◽

Stereoselective Synthesis ◽

Asymmetric Reduction ◽

Cross Coupling ◽

Membered Ring ◽

Stille Reaction ◽

Reaction Sequence ◽

Ring Closing Metathesis ◽

Synthetic Strategy ◽

First Time

A stereoselective synthesis of the dibenzocyclooctadiene lignan core of the natural product schisandrene is described. Starting from readily available gallic acid, the synthetic strategy involves Suzuki–Miyaura cross-coupling, Stille reaction, and ring-closing metathesis (RCM) in the reaction sequence. The required asymmetric center at C-7′ was established by an asymmetric reduction of a keto compound using the Corey–Bakshi–Shibata (CBS) catalyst. In our approach, the eight-membered ring was achieved by RCM for the first time.

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Synthetic Strategies towards Therapeutically Relevant Tailored Macrocycles

Asian Journal of Applied Chemistry Research ◽

10.9734/ajacr/2020/v5i430141 ◽

2020 ◽

pp. 6-20

Author(s):

Ashu Chaudhary ◽

Subhash . ◽

Pinki .

Keyword(s):

Natural Products ◽

Transition Metal ◽

Click Reaction ◽

Cross Coupling ◽

Full Scale ◽

Macrocyclic Compounds ◽

Ring Closing Metathesis ◽

Engineered Systems ◽

Synthetic Approaches

The normally used synthetic approaches toward macrocyclization join full scale lactonization, macrolactamization, transition metal catalysed cross coupling, ring-closing metathesis, and click reaction, among others. Picked continuous examples of macrocyclic synthesis of natural products and druglike macrocycles with noteworthy natural significance are highlighted in each class and outline the general engineered systems for the synthesis of macrocycles. The synthesis of macrocyclic compounds incorporating natural products with differing complexities by ring closing metathesis is depicted. Twelve to huge rings that have been orchestrated in moderate to great yields and the synthesis of larger rings as a part of bi-cyclic or poly-cyclic frameworks are likewise depicted in this review.

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One-step bioengineering of magnetic nanoparticles via a surface diazo transfer/azide–alkyne click reaction sequence

Chemical Communications ◽

10.1039/b716113a ◽

2008 ◽

pp. 621-623 ◽

Cited By ~ 68

Author(s):

Laura Polito ◽

Diego Monti ◽

Enrico Caneva ◽

Eleonora Delnevo ◽

Giovanni Russo ◽

...

Keyword(s):

Magnetic Nanoparticles ◽

Click Reaction ◽

Reaction Sequence ◽

One Step

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Synthesis and biological evaluation of chalcone-triazole hybrid derivatives as 15-LOX inhibitors

Zeitschrift für Naturforschung B ◽

10.1515/znb-2017-0115 ◽

2018 ◽

Vol 73 (2) ◽

pp. 77-83 ◽

Cited By ~ 2

Author(s):

Ali Asadipour ◽

Saeedeh Noushini ◽

Setareh Moghimi ◽

Mohammad Mahdavi ◽

Hamid Nadri ◽

...

Keyword(s):

Aldol Condensation ◽

Click Reaction ◽

Biological Evaluation ◽

Reaction Sequence ◽

Inhibitory Activities ◽

Lox Inhibitors ◽

Synthesis And Biological Evaluation

AbstractAn efficient aldol condensation/click reaction sequence is employed for the synthesis of chalcone-triazole-based derivatives in moderate to good yields. The ability of target compounds to inhibit 15-lipoxygenase enzyme was investigated and moderate to low inhibitory activities were observed for the synthesized compounds.

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A Suzuki Cross-Coupling and Intramolecular Aza-Michael Addition Reaction Sequence Towards the Synthesis of 1,10b-epi-7-Deoxypancratistatins and Their Cytotoxicity Studies

European Journal of Organic Chemistry ◽

10.1002/ejoc.200800830 ◽

2008 ◽

Vol 2008 (34) ◽

pp. 5839-5847 ◽

Cited By ~ 15

Author(s):

Ganesh Pandey ◽

Madhesan Balakrishnan ◽

Pandrangi Siva Swaroop

Keyword(s):

Michael Addition ◽

Addition Reaction ◽

Cross Coupling ◽

Michael Addition Reaction ◽

Reaction Sequence ◽

Cytotoxicity Studies

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Synthesis of 2,3′-spirobi[indolin]-2-ones enabled by a tandem nucleophilic benzylation/C(sp2)–N cross-coupling reaction sequence

Organic & Biomolecular Chemistry ◽

10.1039/c7ob01343d ◽

2017 ◽

Vol 15 (28) ◽

pp. 5887-5892 ◽

Cited By ~ 7

Author(s):

Baodong Cui ◽

Jing Shan ◽

Changlun Yuan ◽

Wenyong Han ◽

Nanwei Wan ◽

...

Keyword(s):

Coupling Reaction ◽

Cross Coupling ◽

Reaction Sequence ◽

Efficient Strategy ◽

Cross Coupling Reaction ◽

New Perspective

This study provides an efficient strategy for the construction of spiro[pyrrolidin-3,2′-oxindoles] and represents a new perspective for the synthesis of spirocyclic oxindoles.

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