One-pot Three-component Coupling Access to 1,2-Dihydropyrrolo[1,2-a]pyrazine-1-phosphonates: Multi-Functionalization of Pyrazine Unit

2021 ◽  
Author(s):  
Jeong Hwa Lee ◽  
Seok Hyun Yoon ◽  
Seonghyeon Nam ◽  
Ikyon Kim
Keyword(s):  
Chemical Space ◽  
One Pot ◽  
Environment Friendly ◽  
Pyrrole Derivative ◽  
Three Component Coupling

A new pyrrolo[1,2-a]pyrazine chemical space with a poly-substituted pyrazine unit was readily accessed by Sc(OTf)3-catalyzed one-pot three-component coupling of pyrrole derivative, amine, and trialkylphosphite under environment-friendly conditions. Formation of multiple...

Metal-, and Organocatalyst-Free One-Pot Assembly of Chiral Aza-Tricyclic Molecules: Creating Six Contiguous Stereocenters from 2-D-Structures and an Amino Acid

2020 ◽  
Author(s):  
Dung Do
Keyword(s):  
Amino Acid ◽  
Chemical Space ◽  
Structural Diversity ◽  
Therapeutic Agents ◽  
Chiral Molecules ◽  
One Pot ◽  
Complex Molecules ◽  
Chiral Catalyst ◽  
Chiral Complex ◽  
Free Process

<p>Chiral molecules with their defined 3-D structures are of paramount importance for the study of chemical biology and drug discovery. Having rich structural diversity and unique stereoisomerism, chiral molecules offer a large chemical space that can be explored for the design of new therapeutic agents.<sup>1</sup> Practically, chiral architectures are usually prepared from organometallic and organocatalytic processes where a transition metal or an organocatalyst is tailor-made for desired reactions. As a result, developing a method that enables rapid assembly of chiral complex molecules under metal- and organocatalyst-free condition represents a daunting challenge. Here we developed a straightforward route to create a chiral 3-D structure from 2-D structures and an amino acid without any chiral catalyst. The center of this research is the design of a <a>special chiral spiroimidazolidinone cyclohexadienone intermediate</a>, a merger of a chiral reactive substrate with multiple nucleophillic/electrophillic sites and a transient organocatalyst. <a>This unique substrate-catalyst (“subcatalyst”) dual role of the intermediate enhances </a><a>the coordinational proximity of the chiral substrate and catalyst</a> in the key Aza-Michael/Michael cascade resulting in a substantial steric discrimination and an excellent overall diastereoselectivity. Whereas the “subcatalyst” (hidden catalyst) is not present in the reaction’s initial components, which renders a chiral catalyst-free process, it is strategically produced to promote sequential self-catalyzed reactions. The success of this methodology will pave the way for many efficient preparations of chiral complex molecules and aid for the quest to create next generation of therapeutic agents.</p>

scholarly journals One-pot three-component synthesis of quinoxaline and phenazine ring systems using Fischer carbene complexes

2010 ◽  
Vol 6 ◽  
Author(s):  
Priyabrata Roy ◽  
Binay Krishna Ghorai
Keyword(s):  
Diels Alder ◽  
Fischer Carbene Complexes ◽  
One Pot ◽  
Carbene Complexes ◽  
Ring Systems ◽  
First Report ◽  
Fischer Carbene ◽  
Carbonyl Derivatives ◽  
Transient Intermediates ◽  
Three Component Coupling

One-pot three-component coupling ofo-alkynylheteroaryl carbonyl derivatives with Fischer carbene complexes and dienophiles leading to the synthesis of quinoxaline and phenazine ring systems has been investigated. This involves the generation of furo[3,4-b]pyrazine and furo[3,4-b]quinoxaline as transient intermediates, which were trapped with Diels–Alder dienophiles. This is the first report on furo[3,4-b]pyrazine intermediates.

An Efficient and Convenient Approach to the Synthesis of Benzopyrans by a Three-Component Coupling of One-Pot Reaction

Synlett ◽  
2003 ◽  
pp. 2001-2004 ◽  
Author(s):  
Tong-Shou Jin ◽  
Jin-Chong Xiao ◽  
Su-Juan Wang ◽  
Tong-Shuang Li ◽  
Xin-Ru Song
Keyword(s):  
One Pot ◽  
Convenient Approach ◽  
Three Component Coupling

scholarly journals A hidden catalysis: metal-, and organocatalyst-free one-pot assembly of chiral aza-tricyclic molecules containing six contiguous stereocenters

2020 ◽  
Author(s):  
Dung Do
Keyword(s):  
Chemical Space ◽  
Structural Diversity ◽  
Therapeutic Agents ◽  
Chiral Molecules ◽  
One Pot ◽  
Complex Molecules ◽  
Chiral Complex ◽  
Enamine Catalysis ◽  
Daunting Challenge

<p></p><p>Chiral molecules with their defined 3-D structures are of paramount importance for the study of chemical biology and drug discovery. Having rich structural diversity and unique stereoisomerism, chiral molecules offer a large chemical space that can be explored for the design of new therapeutic agents.<sup>1</sup> In practice, chiral architectures are usually prepared from organometallic and organocatalytic processes where a transition metal or an organocatalyst is tailor-made for a desired reaction. As a result, developing a method that enables rapid assembly of chiral complex molecules under a metal- and organocatalyst-free condition represents a daunting challenge. Here we developed a straightforward one-pot procedure to create a chiral 3-D structure from 2-D structures and an amino acid without any chiral catalyst. The center of this research is the design of a <a>special chiral spiroimidazolidinone cyclohexadienone intermediate</a>, a merger of a chiral reactive substrate with multiple nucleophillic/electrophillic sites and a transient organocatalyst. <a>This unique substrate-catalyst (“sub-catalyst”) dual role of the intermediate was displayed in its aza-Michael/Michael cascade reaction with an </a>α,β-unsaturated aldehyde under an iminium/enamine catalysis. <a>The enhanced co-ordinational proximity of the chiral substrate and catalyst</a> in the transition state resulted in a substantial steric discrimination and an excellent overall diastereoselectivity. Aza-tricylic molecules with six contiguous stereocenters were assembled from <i>N</i>-alkylated aminophenols, α,β-unsaturated aldehydes and chiral α-amino acids under a hidden “sub-catalysis” where the strategically produced “sub-catalyst” does not present in initial components of the reaction. The success of this methodology will pave the way for many efficient preparations of chiral complex molecules.</p><br><p></p>

ChemInform Abstract: Three-Component Coupling of Acylphosphonates and Two Carbonyl Compounds Promoted by Low-Valent Samariums: One-Pot Synthesis of β-Hydroxyphosphonates.

ChemInform ◽  
2010 ◽  
Vol 31 (18) ◽  
pp. no-no
Author(s):  
Ken Takaki ◽  
Yuichiro Itono ◽  
Akihiro Nagafuji ◽  
Yoji Naito ◽  
Tetsuya Shishido ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
One Pot ◽  
One Pot Synthesis ◽  
Low Valent ◽  
Three Component Coupling

An efficient approach towards three component coupling of one pot reaction for synthesis of functionalized benzopyrans

2006 ◽  
Vol 43 (6) ◽  
pp. 1691-1693 ◽  
Author(s):  
B. Sunil Kumar ◽  
N. Srinivasulu ◽  
R. H. Udupi ◽  
B. Rajitha ◽  
Y. Thirupathi Reddy ◽  
...  
Keyword(s):  
One Pot ◽  
Efficient Approach ◽  
Three Component Coupling

One-pot Synthesis of 3-Substituted-3-Hydroxyindolin-2-ones: Three Component Coupling of N-Protected isatin, Aryne Precursor and 1, 3-Cyclodione under Metal-free Conditions

2021 ◽  
Author(s):  
Hemanta Hazarika ◽  
Babulal Das ◽  
Kangkana Chutia ◽  
Pranjal Gogoi
Keyword(s):  
One Pot ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Three Components ◽  
Three Component Coupling

An aryne-based synthetic protocol has been developed for the synthesis of 3-substituted-3-hydroxy-indolin-2-ones. A wide variety of 3-hydroxyindolin-2-ones were synthetized in good yields under metal-free conditions via three components coupling of...

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