A Domino Approach for the Synthesis of 4-Carboxamide Oxazolines from Azirines

Synthesis ◽  
2021 ◽  
Author(s):  
Ali Nikbakht ◽  
Fariba Mohammadi ◽  
Mohammad Sadeq Mousavi ◽  
Kamran Amiri ◽  
Saeed Balalaie ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Ring Expansion ◽  
Target Product ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Forming Efficiency ◽  
High Bond ◽  
Ring Expansion Reaction ◽  
Indium Catalyst

A regio- and the diastereoselective ring-expansion reaction of N-acyl aziridine has been described for the synthesis of 4-carboxamide oxazolines using InCl3. A domino Ugi-Joullié/ring expansion reaction of arylphenylazirines, isocyanides, and carboxylic acids led to the target product through N-acylaziridine intermediate in the presence of indium catalyst. The oxazolines were synthesized in moderate to excellent yields with high atom-economy and high bond-forming efficiency under mild reaction conditions.

Synthesis of 3-Oxoisoindoline-1-carboxamides through Sequential Four-Component Ugi Reaction/Oxidative Nucleophilic Substitution of Hydrogen

Synlett ◽  
2020 ◽  
Vol 31 (09) ◽  
pp. 861-865
Author(s):  
Saeed Balalaie ◽  
Ahmed Al-Harrasi ◽  
Kamran Amiri ◽  
Muhammad U. Anwar
Keyword(s):  
Nucleophilic Substitution ◽  
Aerobic Oxidation ◽  
Ugi Reaction ◽  
Nucleophilic Substitution Of Hydrogen ◽  
Reaction Conditions ◽  
Bond Forming ◽  
Reaction Proceeds ◽  
Forming Efficiency ◽  
High Bond ◽  
Directing Group

This paper describes a diversity-oriented approach to the formation of 3-oxoisoindoline-1-carboxamide derivatives utilizing the potential of the nitro group as a directing group. The reaction proceeds through a novel class of post-transformation reactions through a sequential four-component Ugi reaction/oxidative nucleophilic substitution of hydrogen. The 3-oxoisoindoline-1-carboxamide derivatives were synthesized in the presence of a base under mild reaction conditions with high regio- and chemoselectivity. The aerobic oxidation, high bond-forming efficiency, high atom economy, and good to excellent yields are the main advantages of this approach.

Some Derivatives of 1-Benzazepine. Part II

1974 ◽  
Vol 52 (4) ◽  
pp. 610-615 ◽  
Author(s):  
G. R. Birchall ◽  
A. H. Rees
Keyword(s):  
Carboxylic Acids ◽  
Ring Expansion ◽  
Hydrazoic Acid ◽  
Ring Contraction ◽  
Effect Of Substituents ◽  
Ring Expansion Reaction ◽  
Derivatives Of

We have investigated the ring expansion of some substituted 1,4-naphthoquinones by hydrazoic acid to yield new 1-benzazepine derivatives of the "azatropolone" type. Ring contraction of those products, which are 2,5-dihydro-3-hydroxy-2,5-dioxo-1-benzazepines, gives 4-quinolone-2-carboxylic acids. Some of the reactions of the new benzazepine system were investigated. Attempts to prepare substituted derivatives suitable for making 1-benzazatrop-5-one were not successful.The effect of substituents on the ring expansion reaction is discussed and an anomalous ring expansion to a 2,5-dihydro-4-hydroxy-2,5-dioxo-1-benzazepine is described and explained mechanistically.

A one-pot synthesis of [1,2,3]triazolo[1,5-a]quinoxalines from 1-azido-2-isocyanoarenes with high bond-forming efficiency

2017 ◽  
Vol 53 (7) ◽  
pp. 1305-1308 ◽  
Author(s):  
Dengke Li ◽  
Tingting Mao ◽  
Jinbo Huang ◽  
Qiang Zhu
Keyword(s):  
One Pot ◽  
Efficient Approach ◽  
Bond Forming ◽  
One Pot Synthesis ◽  
Forming Efficiency ◽  
High Bond ◽  
Terminal Acetylenes

An efficient approach to prepare 1,2,3-triazolo[1,5-a]quinoxaline scaffolds, starting from 1-azido-2-isocyanoarenes and terminal acetylenes or substituted acetaldehydes, has been developed.

Microwave Induced Green chemistry approach towards synthesis of heterocyclic compounds via C-N Bond Forming Reactions

2021 ◽  
Vol 08 ◽  
Author(s):  
Bimal Krishna Banik ◽  
Biswa Mohan Sahoo ◽  
BVV Ravi Kumar ◽  
Krishna Chandra Panda
Keyword(s):  
Green Chemistry ◽  
Ring Opening ◽  
Heterocyclic Compounds ◽  
Unique Feature ◽  
Ring Closure ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Formation Reaction ◽  
Bond Forming ◽  
Bond Forming Reactions

: The synthesis of heterocyclic compounds via carbon-nitrogen (C-N) bond formation reaction is considered as an emerged and efficient protocol in the field of synthetic chemistry. The C–N bond-forming reactions can proceed through condensation, coupling, ring-opening, cyclization or ring closure process etc. The reactivity pattern of these reactions mainly depends upon the reaction conditions as well as the type of catalysts and reacting substances that are associated with the synthesis of heterocyclic compounds containing the C-N system including pyrazole, imidazole, pyridine, pyrimidine, thiazole, tetrazole, isoxazole, benzothiazine and benzimidazole etc. Further, the technique of microwave-induced synthesis becomes an alternative strategy for the sustainable production of structurally diverse organic compounds. This method provides a cleaner reaction, faster reaction rate, atom economy and energy-efficient. So, the utilization of microwave radiation in organic synthesis becomes resource-friendly and eco-friendly processes. It follows the green chemistry approach by using safer solvents, renewable starting materials and green catalysts. The unique feature of this method is to generate various types of bioactive or medicinal agents.

Catalyst-Free Synthesis of Fused Triazolo-Diazepino[5,6-b]Quinoline Derivatives via a Sequential Ugi-4CR–Nucleophilic Substitution–Intramolecular Click Reaction

Synlett ◽  
2018 ◽  
Vol 29 (08) ◽  
pp. 1095-1101 ◽  
Author(s):  
Saeed Balalaie ◽  
Aref Vaezghaemi ◽  
Nahid Zarezadeh ◽  
Frank Rominger ◽  
Hamid Bijanzadeh
Keyword(s):  
Nucleophilic Substitution ◽  
Click Reaction ◽  
Quinoline Derivatives ◽  
Wide Scope ◽  
Bond Forming ◽  
Catalyst Free ◽  
Forming Efficiency ◽  
High Bond

A convenient, post-transformational reaction has been ­developed for the construction of highly diversified quinoline-fused triazolo-diazepinones featuring four diversification points by employing a catalyst-free Ugi four-component–nucleophilic substitution–intra­molecular click cycloaddition sequence. This approach provides a wide scope of products with good yields and high bond-forming efficiency.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

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