Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines

Synthesis ◽  
2020 ◽  
Vol 52 (10) ◽  
pp. 1512-1522
Author(s):  
Alexander Yu. Rulev ◽  
Alexey R. Romanov ◽  
Alexander V. Popov ◽  
Evgeniy V. Kondrashov ◽  
Sergey V. Zinchenko
Keyword(s):  
Intramolecular Cyclization ◽  
Michael Addition ◽  
High Selectivity ◽  
Reaction Path ◽  
Cascade Reactions ◽  
Trifluoromethyl Group ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
High Yields

A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles in high yields (up to 99%). The unique influence of trifluoromethyl group on the reaction path is demonstrated.

Efficient method for the synthesis of polysubstituted 2,6-dicyanoanilines by one-pot three-component tandem reaction of malononitrile with α,β-unsaturated imines

2015 ◽  
Vol 69 (7) ◽  
Author(s):  
Wei Chen ◽  
Xiao-Yan Lu
Keyword(s):  
Efficient Method ◽  
Michael Addition ◽  
Tandem Reaction ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
High Yields ◽  
The Michael Addition

AbstractA facile and efficient one-pot synthesis of polysubstituted benzenes was achieved via the Michael addition of malononitrile with α,β-unsaturated imines and a sequential tandem reaction. This reaction generates polysubstituted 2,6-dicyanoanilines in high yields (15 examples, isolated yields of 57-91 %), and proceeds under mild reaction conditions (60°C, 10 min). In addition, a possible mechanism accounting for the reaction is proposed.

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 Mild and Efficient One Pot Synthesis of Imidazolinesand Benzimidazoles from Aldehydes

2007 ◽  
Vol 4 (4) ◽  
pp. 606-610 ◽  
Author(s):  
Rajesh Kumar ◽  
Y. C. Joshi
Keyword(s):  
Ammonium Nitrate ◽  
Column Chromatography ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
High Yields

A series of some imidazolines and benzimidazoles were synthesizedfrom various aldehydes and 1,2-diamines in the presence of ceric(IV)ammonium nitrate (CAN). The title compounds were prepared via one stepsynthesis method. The simplicity of the reaction conditions with shorterreaction time and with out use of column chromatography to get the pureproducts in high yields makes this method more attractive for organic chemists.

Construction of Functionalized (Dihydro)thieno[2,3-c]chromene Derivatives via a Domino Michael Addition/Intramolecular Cyclization Reaction

Synthesis ◽  
2018 ◽  
Vol 50 (08) ◽  
pp. 1667-1674
Author(s):  
Jian-Wu Xie ◽  
Li-Si-Han Yu ◽  
Jian-Lian Dong ◽  
Zhi-Jian Gao ◽  
Jing Wang
Keyword(s):  
Intramolecular Cyclization ◽  
Michael Addition ◽  
Lewis Base ◽  
Cyclization Reaction ◽  
One Pot ◽  
One Pot Synthesis

A one-pot synthesis of substituted (dihydro)thieno[2,3-c]chromene derivatives was developed through a Lewis base catalyzed domino Michael addition/intramolecular cyclization reaction between 3-nitro-2H-chromenes and thioamides. The desired (dihydro)thieno[2,3-c]chromene derivatives were prepared with a large substrate scope (22 examples) and excellent diastereoselectivity in moderate to excellent yields.

Two Efficient One-Pot Approaches for Regioselective Synthesis of New 3-Arylpyridazino[4,3-c]quinolin-5(6H)-ones

2015 ◽  
Vol 68 (10) ◽  
pp. 1529 ◽  
Author(s):  
Mehdi Rimaz
Keyword(s):  
Hydrazine Hydrate ◽  
Regioselective Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
The One ◽  
High Yields ◽  
Arylglyoxal Monohydrates ◽  
Operational Simplicity

Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.

Iodine-Mediated Multi-Component Reactions: Readily Access to Tetrazoles and Guanidines

2020 ◽  
Vol 17 ◽  
Author(s):  
Bajivali Shaik ◽  
Mohan Seelam ◽  
Ramana Tamminana ◽  
Prasad Rao Kammela
Keyword(s):  
Reaction Time ◽  
Benzoyl Chloride ◽  
Functional Group ◽  
Molecular Iodine ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
One Pot ◽  
Short Reaction Time ◽  
One Pot Synthesis ◽  
High Yields

Abstract: Environmentally benign syntheses of One-pot sequential reactions of benzoyl chloride with amines followed by the treatment of molecular I2 reagent under basic conditions provide benzoyl tetrazoles and guanidines in moderate to excel-lent yields. This one-pot synthesis has several advantages such as mild reaction conditions, short reaction time, convenient workup, high yields, using cheap and readily available reagent molecular Iodine. In addition, functional group tolerance has been explored

Sign in / Sign up

Export Citation Format

Share Document