scholarly journals Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

2016 ◽  
Vol 12 ◽  
pp. 2204-2210 ◽  
Author(s):  
Xiaofeng Zhang ◽  
Kenny Pham ◽  
Shuai Liu ◽  
Marc Legris ◽  
Alex Muthengi ◽  
...  

The one-pot [3 + 2] cycloaddition of an azomethine ylide with a maleimide followed by another [3 + 2] cycloaddition of an azide with the second maleimide gives a 1,5-diamino intermediate which is used for a sequential aminomethylation reaction with formaldehyde through [5 + 1] annulation to afford a novel polycyclic scaffold bearing tetrahydroquinazoline, pyrrolidine, pyrrolidinedione, and N-substituted maleimide in stereoselective fashion.

2020 ◽  
Vol 10 (3) ◽  
pp. 269-276
Author(s):  
Immo Serbian ◽  
Erik Prell ◽  
Ahmed Al-Harrasi ◽  
Rene Csuk

The one-pot reaction of per-acetylated glycopyranosyl bromides with alcohols in light-protected flask leads to the stereoselective synthesis of deacetylated alkyl pyranosides in good yields.


2017 ◽  
Vol 41 (2) ◽  
pp. 873-878 ◽  
Author(s):  
Adinarayana Murthy Akondi ◽  
Sowmya Mekala ◽  
Mannepalli Lakshmi Kantam ◽  
Rajiv Trivedi ◽  
L. Raju Chowhan ◽  
...  

We report here an efficient protocol for the one-pot facile synthesis of spiro[indeno[1,2-b]quinoxaline-11,3′-pyrrolizine]heterocyclic scaffolds and their AChE inhibitory studies.


2020 ◽  
Vol 7 (18) ◽  
pp. 2664-2669
Author(s):  
Ni-Ni Zhou ◽  
Si-Si Ning ◽  
Lin-Qiang Li ◽  
Jie-Yun Zhang ◽  
Ming-Jin Fan ◽  
...  

The one-pot synthesis of dibenzo[a,f]azulen-12-ones has been established starting from o-propargyl alcohol benzaldehydes and alkynes.


ChemInform ◽  
2010 ◽  
Vol 33 (23) ◽  
pp. no-no
Author(s):  
Gowravaram Sabitha ◽  
Erigala Venkata Reddy ◽  
Jhillu S. Yadav

Synthesis ◽  
2002 ◽  
Vol 2002 (03) ◽  
pp. 409-412 ◽  
Author(s):  
Gowravaram Sabitha ◽  
Erigala Venkata Reddy ◽  
Jhillu S. Yadav

2021 ◽  
Author(s):  
Alessandra Casnati ◽  
Dawid Lichosyt ◽  
Bruno Lainer ◽  
Lukas Veth ◽  
Pawel Dydio

One-pot multi-step procedures bear the potential to rapidly build up molecular complexity while avoiding the wasteful and costly isolations and purifications of consecutive intermediates. Here we report multi-catalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Because each transformation of the sequence is executed by an independent catalyst, without any catalytic cross-reactivity, allylic alcohols bearing a prochiral double bond can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er and >20:1 dr). Overall, with the aid of up to four catalysts operating in a single vessel, the protocols directly convert simple starting materials into a range of value-added products with high stereocontrol and excellent material efficiency, demonstrating both the efficacy and the advantages of the one-pot synthesis employing multiple transition-metal catalysts.


2021 ◽  
Author(s):  
Alessandra Casnati ◽  
Dawid Lichosyt ◽  
Bruno Lainer ◽  
Lukas Veth ◽  
Pawel Dydio

One-pot multi-step procedures bear the potential to rapidly build up molecular complexity while avoiding the wasteful and costly isolations and purifications of consecutive intermediates. Here we report multi-catalytic protocols that convert alkenes, unsaturated aliphatic alcohols, and aryl boronic acids into secondary benzylic alcohols with high stereoselectivities under sequential catalysis that integrates alkene cross-metathesis, isomerization, and nucleophilic addition. Because each transformation of the sequence is executed by an independent catalyst, without any catalytic cross-reactivity, allylic alcohols bearing a prochiral double bond can be converted to any stereoisomer of the product with high stereoselectivity (>98:2 er and >20:1 dr). Overall, with the aid of up to four catalysts operating in a single vessel, the protocols directly convert simple starting materials into a range of value-added products with high stereocontrol and excellent material efficiency, demonstrating both the efficacy and the advantages of the one-pot synthesis employing multiple transition-metal catalysts.


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