Intramolecular Cyclization of N-Allyl Propiolamides: a Facile Synthetic Route to Highly Substituted G- Cite This: RSC Adv.,2017,7, 28407 Lactams (A Review)
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RSC Advances View Article Online REVIEW View Journal | View Issue Intramolecular cyclization of N-allyl propiolamides: a facile synthetic route to highly substituted g- Cite this: RSC Adv.,2017,7, 28407 lactams (a review) Somayeh Soleimani-Amiri,*a Esmail Vessally, b Mirzaagha Babazadeh,c Akram Hosseiniand and Ladan Edjlalic The development of simple and efficient methods for construction of substituted g-lactams is an important synthetic goal because such ring skeletons are present in numerous natural compounds that display diverse Received 15th March 2017 biological activities. Intramolecular cyclization of N-allyl propiolamides is an efficient, economic, and Accepted 4th May 2017 operationally simple strategy for the synthesis of the titled compounds. In the present review we will DOI: 10.1039/c7ra03075d discuss recent advances in the synthesis of functionalized g-lactam derivatives from these easily rsc.li/rsc-advances accessible and versatile building blocks with the emphasis on the mechanistic aspects of the reactions. Creative Commons Attribution 3.0 Unported Licence. 1. Introduction supplement that has the ability to enhance memory and learning ability. It also used as an adjunctive treatment for 2 Needless to say, g-lactams are at the heart of a number of myoclonus of cortical origin. Marizomib 3 is a naturally- medicinally and biologically important compounds, as well as occurring salinosporamide, isolated from the marine actino- a large array of natural products. For instance, brivaracetam 1, mycete Salinospora tropica. This compound is a promising drug with the brand name Briviact, is an anticonvulsant drug mar- candidate for the treatment of multiple myeloma and mantle 3,4 keted worldwide for the treatment of partial onset seizures.1 cell lymphoma. Annosqualine 4, which has good antibacterial Piracetam 2 (also known as a smart drug) is a nootropic activity, is a natural product isolated from the stems of Annona 5,6 This article is licensed under a Squamosa. Codinaeopsin 5, which was isolated from an endophytic fungus collected in Costa Rica, has signicant a Department of Chemistry, Karaj Branch, Islamic Azad University, Karaj, Iran. E-mail: 7 [email protected]; [email protected] antimalarial activity. This biological activity has made the b synthesis of g-lactams quite attractive, and a large number of Open Access Article. Published on 30 May 2017. Downloaded 9/23/2021 11:40:53 PM. Department of Chemistry, Payame Noor University, Tehran, Iran cDepartment of Chemistry, Tabriz Branch, Islamic Azad University, Tabriz, Iran straightforward and robust methods for the construction of 8–12 dDepartment of Engineering Science, College of Engineering, University of Tehran, P. O. these cores has been established. More recently, Rivas and Box 11365-4563, Tehran, Iran Somayeh Soleimani-Amiri was Esmail Vessally was born in born in Tehran, Iran, in 1975. Sharabiyan, Sarab, Iran, in She received her B.S. degree in 1973. He received his B.S. degree Pure Chemistry from Shahid in Pure Chemistry from Univer- Beheshti University, Tehran, sity of Tabriz, Tabriz, Iran, and Iran, and her M.S. degree in his M.S. degree in organic organic chemistry from Alzahra chemistry from Tehran Univer- University, Tehran, Iran, in sity, Tehran, Iran, in 1999 under 2002 under the supervision of the supervision of Prof. H. Pir- Prof. S. H. Abdi Oskooie and elahi. He completed his Ph.D. Prof. M. M. Heravi. She degree in 2005 under the super- completed his Ph.D. degree in vision of Prof. M. Z. Kassaee. 2009 under the supervision of Now he is working at Payame Prof. M. Z. Kassaee. Now she is working at Karaj Branch, Islamic Noor University as full Professor of Organic Chemistry. His Azad University as Assistant Professor. Her research interests research interests include Theoretical Organic Chemistry, new include Computational Organic Chemistry, Nano Chemistry, methodologies in organic synthesis and spectral studies of organic Synthesis of Organic Compounds. compounds. This journal is © The Royal Society of Chemistry 2017 RSC Adv.,2017,7,28407–28418 | 28407 View Article Online RSC Advances Review Ling published an interesting review paper that covers most of 2. Transition metal-catalyzed the recent advances in the synthesis of the titled compounds.12 However, synthesis of these cores through intramolecular cyclizations cyclization of simple and easily accessible N-allyl propiolamide 2.1 Palladium derivatives was omitted, while this synthetic strategy has Synthesis of g-lactams via Pd-catalyzed intramolecular cycliza- ffi recently attracted much attention because of its high e ciency, tion of propiolamide derivatives has been the subject of atom economy, and operational simplicity (Fig. 1). a number of papers. One of the earliest report on this chemistry In connection with our series of review papers on the have been published by Lu and co-workers in 1996. They synthesis of nitrogen based heterocycles from N- showed that treatment of N-allyl propiolamides 6 with the propargylamine/amide derivatives,13–22 we summarize here PdCl2(PhCN)2/CuCl2/LiCl system in acetonitrile directly gave g a variety of protocols for the synthesis of -lactam cores from corresponding a-chloromethylene-b-chloromethyl-g-lactams 7 readily accessible N-allyl propiolamides. The review is divided aer 6–40 hours at room temperature (Scheme 1). According to into two major sections. The rst section focuses exclusively on the author proposed mechanism, this transformation pro- transition metal-catalyzed cyclization of N-allyl propiolamides, ceeded via a chloropalladation/oxidative cleavage/insertion while the second covers radical promoted cyclizations. It should sequential process.23 In a closely related study, the same be noted that we have not discussed synthesis of indolinones group found that N-(30-formylallylic)propiolamides 8 were con- g (benzene-fused -lactams), since it has recently been described verted to the corresponding a-bromomethylene-b-for- in another publication.13 mylmethyl-g-lactams 9, via Pd(II)-catalyzed intramolecular cyclization using LiBr as bromide source in HOAc at room temperature (Scheme 2).24 Mirzaagha Babazadeh is Asso- In 2005, Zhu and Zhang described the rst PdCl2-catalyzed ciate Professor of Organic Chem- cis-chloropalladation-cyclization reaction of N-allyl propiola- Creative Commons Attribution 3.0 Unported Licence. 10 istry in Department of Chemistry mides. Thus, the treatment of 1,6-enyne substrates with 5 ff a at Tabriz Branch, Islamic Azad mol% of PdCl2 in HOAc at 50 Ca orded corresponding (E)- - g 11 University, Tabriz, Iran. He was halomethylene- -lactams in high isolated yields g born in Tabriz, Iran, in 1973. He (Scheme 3a). The mechanism proposed for the formation of - lactams 11 involves the key intermediate A, which underwent received his B.S. degree in 25 Applied Chemistry (1996) and dehalopalladation to produce the cyclized product. Subse- his M.S. degree in Organic quently, the same authors extended this chemistry to synthesis a g 13 Chemistry from University of of -phenylmethylene- -lactams via a beautiful Pd(0)- catalyzed tandem cyclization/Suzuki coupling reaction of N- This article is licensed under a Tabriz, Tabriz, Iran (1999) under 12 26 the supervision of Prof. A. A. allyl propiolamides with phenylboronic acid. Several cata- lysts, bases and solvents were tested, and the system Pd(PPh3)4/ Entezami and Prof. H. Namazi. 27 He completed his Ph.D. degree under the supervision of Prof. K. D. KF/toluene was found to be superior. Under optimized Open Access Article. Published on 30 May 2017. Downloaded 9/23/2021 11:40:53 PM. Safa in University of Tabriz, Tabriz, Iran (2005). His research conditions, the reaction tolerates both aryl and alkyl substituted 13 interests focus on organic synthesis, catalyst, polymer, green internal propiolamides and gave the corresponding lactams chemistry, drug delivery systems, organosilicon compounds and in high yields (Scheme 3b). nanocomposites. Akram Hosseinian was born in Ladan Edjlali was born in Ahar, Iran, in 1973. She received Tabriz, Iran, in 1960. She her B.S. degree in Pure Chem- received her B.S. degree in istry from University of Tehran, Applied Chemistry from Univer- Iran, and her M.S. degree in sity of Tabriz, Iran, and her M.S. inorganic chemistry from Tarb- degree in organic chemistry from iat Modares University, Tehran, University of Tabriz, Tabriz, Iran, in 2000 under the super- Iran, in 1993 under the super- vision of Prof. A. R. Mahjoub. vision of Prof. Y. Mirzaei. She She completed his Ph.D. degree completed his Ph.D. degree in in 2007 under the supervision of 2000 under the supervision of Prof. A. R. Mahjoub. Now she is Prof. Y. Mirzaei and Prof. S. M. working at University of Tehran Golabi. Now, she is working at as Assistant Professor. Her research interests include inorganic Islamic Azad University, Tabriz Branch as Associate Professor. Her and organic synthesis, new methodologies in nano material research interests include organic synthesis and new methodolo- synthesis. gies in organic synthesis. 28408 | RSC Adv.,2017,7,28407–28418 This journal is © The Royal Society of Chemistry 2017 View Article Online Review RSC Advances Fig. 1 Selected examples of bioactive g-lactams. Creative Commons Attribution 3.0 Unported Licence. This article is licensed under a Scheme 1 a b g Open Access Article. Published on 30 May 2017. Downloaded 9/23/2021 11:40:53 PM. Lu's synthesis of -chloromethylene- -chloromethyl- -lactams 7. trans-acetoxypalladation/b-heteroatom elimination sequential process. The author found that when the reaction was carried out in the presence of chiral nitrogen-containing ligands, an asymmetric version of this protocol with moderate enantiose- lectivity was established.28 In 2010, the same group reported an elegant approach for the synthesis of a-alkylidene-b-hydroxy-g-lactams 18 via Pd(II)- catalyzed cascade reaction of propiolamides 16 and arylboronic acids 17. The optimum conditions for this reaction utilize Pd(OAc)2 as the catalyst, bpy as ligand and DCE/H2O (20 : 1) as 0 Scheme 2 Pd(II)-catalyzed cyclization of N-(3 -formylallylic)propio- solvent.