Nitrogen-containing heterocycle synthesis

Molina, P., Vilaplana, M. J. Iminophosphoranes useful building blocks for the preparation of nitrogen-containing heterocycles. Synthesis 1994,1197-1218. 

Haloaniline derivatives are widely available from chemical suppliers and have been applied extensively in nitrogen-containing heterocycle synthesis. Additionally, 2-haloanilines can act as 1,2-dihaloarene precursors as well in the Sandmeyer reaction. As bully chemicals, anilines are usually applied as substrates for the synthesis of 2-haloanilines after halogenation. 

Kalinin AA, Mamedov VA, YaniUdn VV, Nastapova NV, Rizvanov IKh, Morozov VI (2009) Macrocycles, derivatives of nitrogen-containing heterocycles Synthesis and electrochemical properties of diindolizinadiquinoxalinacyclooxaalkaphanes. Russ Chem Bull, Int Ed 58 (7) 1484-1492. doi 10.1007/sl 1172-009-0200-6... 

The 4-unsaturated-5-oxazolones provide convenient starting materials for the synthesis of other nitrogen-containing heterocyclic systems. The preparation of tetrazoles and isoquinolines is discussed in Sections II,B, 1 and II,B,2,b. 

Microwave-Assisted Synthesis of Sulfur and Nitrogen-Containing Heterocycles... 

Besson T, Thiery V (2006) Microwave-Assisted Synthesis of Sulfur and Nitrogen-Containing Heterocycles. 1 59-78... 

Chalcone dibromides are advantageous intermediates for the preparation of various nitrogen-containing heterocycles (refs. 1-4). In the case of exocyclic a,P-unsaturated ketones, however, only few examples are known concerning the utilization of their dibromides for such purposes (ref. 5). Our aim was, therefore, the synthesis of the dibromides of various exocyclic a,P-unsaturated ketones (ref. 6) and to study their chemical transformations. In our present paper the reaction of such dibromides with azide nucleophile is reported. 

This method is the basis for synthesis of nitrogen-containing heterocyclic compounds when Z is a carbonyl-containing substituent.290... 

The synthesis of nitrogen containing heterocyclic systems by photocylo-addition processes is virtually limited to examples involving [ 2 + 2] cycloaddition of imines, nitriles, and azo compounds. Successful additions are few in number and the requirements for success uncertain. The reactions do not proceed with the facility with which carbonyl containing compounds undergo photocycloaddition to alkenes to give oxetans, and various explanations have been advanced to account for this observed lack of reactivity.226... 

Strecker reactions provide one of the most efficient methods for the synthesis of a-amino nitriles, which are useful intermediates in the synthesis of amino acids and nitrogen-containing heterocycles. Although classical Strecker reactions have some limitations, use of trimethylsilyl cyanide (TMSCN) as a cyano anion source provides promising and safer routes to these compounds.133-351 Consequently, we focused our attention on tributyltin cyanide (Bu3SnCN), because Bu3SnCN is stable in water and is also a potential cyano anion source. Indeed, the Strecker-type reactions of aldehydes, amines, and Bu3SnCN proceeded smoothly in water (Eq. 9).1361 It should be noted that no surfactants are required in this reaction. Furthermore, Complete recovery of the toxic tin compounds is also possible in the form of bis(tributyltin) oxide after the reaction is over. Since conversion of bis(tributyltin) oxide to tributyltin cyanide is known in the literature, this procedure provides a solution to the problem associated with toxicity of tin compounds. 

The synthesis of oxygen- and nitrogen-containing heterocyclic compounds by anionic cyclization of unsaturated organolithium compounds has been reviewed recently. " Broka and Shen reported the first intramolecular reaction of an unstabilized a-amino-organolithium compound using reductive lithiation of an A,5-acetal derived from a homoaUylic secondary amine (Scheme 21). Just one example was reported treatment with lithium naphthalenide gave the pyrrolidine product, predominantly as the cis isomer. 

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