Fathi Vavsari, V. ; Balalaie, S.

Annulation of 2-alkynylbenzamides: The versatile chemical compounds

In Targets in Heterocyclic Systems, 2021, Vol 25, 426-438.

2-Alkynylbenzamides as versatile substrates have been widely used as precursors for the synthesis of Nitrogen and Oxygen atoms containing heterocycles. The focus of this mini-review is on the introduction of 2-alkynylaniline and its derivatives in the synthesis of five-, six-, and seven-membered heterocycles including indoles, fused indoles, isoindolinones, benzoisofurans, isochromens, isocoumarins, isoquinolines, isoquinolinones, quinolones, and azepinones.

Balalaie, S.; Shakeri, P.

Post-Ugi Transformation of N-substituted-2-alkyneamides for the Construction of Diverse Heterocyclic Scaffolds

In Targets in Heterocyclic Systems-chemistry and Properties, 2018, Vol 22, 468-489.

Post-Ugi transformation reactions are well known to form molecular complexity, fused heterocyclic backbones. Existence of alkyne moiety in the structure of Ugi-4CR products allows post condensation cyclizations establishing carbon-carbon bonds by means of metal-catalyzed reactions or metal-free reactions. Synthesis of different heterocyclic backbones such as 2-oxindoles and spiroindolines can be constructed based on alkyne cyclization of post-Ugi reaction.

Alavijeh, N.S.; Ahadi, S.; Balalaie, S.

Multicomponent Reactions of Amino Acids and their Derivatives in Heterocycle Chemistry

In Multicomponent Reactions, CRC Publisher, 2017, 83-111.

This chapter summarizes multicomponent reactions based on amino acids and their derivatives in the heterocycles chemistry. It provides the classification of multicomponent reactions of amino acids and derivatives according to the ring size of heterocyclic compounds in five categories: Four-membered heterocycles, Five-membered heterocycles, Six-membered heterocycles, Seven-membered heterocycles and fused heterocycles. Chiral β-amino acids constitute interesting building blocks for the synthesis of chiral β-lactams. One of the recent reports on this concept is the synthesis of conformationally constrained tricyclic β-lactam enantiomers through Ugi four-center, three-component reactions of a monoterpene-based β-amino acid. The chapter discusses the synthesis of β-lactam peptidomimetics through Ugi MCR. It describes the stereoselective synthesis of fully substituted tetrahydrofurans through 1, 3-dipolar cycloaddition with cinnamaldehydes. The chapter focuses on the occurrence of an oxidative pathway mediated by highly reactive 2(1H)pyrazinoium salts leads to the first direct preparative method for the straightforward assembly of diversely decorated pyrazin-2,3-(1H,4H)-diones.

Alavijeh, N. S.; Ghabraie, E.; Balalaie, S.

Reactions Involving an α,β-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron, Silicon, Free - Radical and Metal - Mediated Reactions

Multicomponent Reaction 2. Thieme Verlag, Stuttgart. Science of Synthesis. 2014.

This chapter describes various multicomponent reactions (MCRs) involving in situ generated α,β-unsaturated carbonyl compounds formed by Wittig-type reactions.The synthesis of α,β -unsaturated carbonyl compounds is of great importance as this bifunctional unit is a key structural component in a variety of naturally occurring and biologically essential substances. Moreover, due to their high reactivity toward nucleophiles, α,β -unsaturated ketones are very valuable intermediates in the synthesis of pharmaceutical compounds, natural products, and other functional substances. α,β –Unsaturated carbonyl compounds have been synthesized using various methods based on the formation of the C=C bond and, among these methods, Wittig-type reactions still occupy a prominent position. Wittig reactions involve the synthesis of an alkene by reaction of a carbonyl compound (aldehyde or ketone) with a phosphonium ylide, via either a betaine and/or an oxaphosphetane intermediate.

Balalaie, S.; Golmohammadi, F.; Shakeri, P.

Peptide Chemistry (Basics, Synthesis and Application)

K. N. Toosi University Press, 2020.