Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems

• Alexander F. Khlebnikov,
• Mikhail S. Novikov,
• Viktoriia V. Pakalnis,
• Roman O. Iakovenko and
• Dmitry S. Yufit

Beilstein J. Org. Chem. 2014, 10, 784–793, doi:10.3762/bjoc.10.74

• routes of bis[1,3]oxazino[3,2-a:3′,2′-d]pyrazine skeleton formation revealed a new domino reaction of 3-aryl-2H-azirines occurring in the presence of furandiones: acid-catalyzed dimerization to dihydropyrazine followed by consecutive cycloaddition of the latter to two molecules of acylketenes. Keywords

• : acylketene; azirine; domino reaction; furandione; Introduction 2H-Azirines, the most strained nitrogen unsaturated heterocyclic systems, are versatile building blocks for the construction of various heterocyclic nitrogen-containing compounds. Because 2H-azirines contain an activated C=N double bond and a

Four-component reaction of cyclic amines, 2-aminobenzothiazole, aromatic aldehydes and acetylenedicarboxylate

• Hong Gao,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 2934–2939, doi:10.3762/bjoc.9.330

• : benzothiazole; domino reaction; electron-deficient alkyne; multicomponent reaction; pyrrolidinone; Introduction Over fifty years ago, Huisgen firstly described the addition reactions of nitrogen-containing heterocycles to electron-deficient alkynes to form 1,4-dipolar intermediates, which can reacted

Flexible synthesis of anthracycline aglycone mimics via domino carbopalladation reactions

• Markus Leibeling and
• Daniel B. Werz

Beilstein J. Org. Chem. 2013, 9, 2194–2201, doi:10.3762/bjoc.9.258

• different products and a broad range of structural diversity. Keywords: anthracyclines; carbohydrates; carbopalladation; catalysis; domino reaction; natural products; Introduction Anthracyclines are a widespread class of natural products which belong to the group of aromatic polyketides [1]. Most of them

• The choice of the right diyne is crucial for a successful synthesis of the target compound. Preliminary investigations had shown that both dialkynes with benzylic hydroxy functionalities and 1,2-bis(2-propynyl)benzene did not yield viable results in the domino reaction. The selective installation of

• materials for the synthesis of 23e. Silyl ether formation and domino reaction The union between both building blocks proved to be more difficult than originally envisioned. During our previous studies of chromans and isochromans the implementation of ether linkages afforded good results. The synthesis of

Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

• Koichiro Miyazaki,
• Yu Yamane,
• Ryuichiro Yo,
• Hidemitsu Uno and
• Akio Kamimura

Beilstein J. Org. Chem. 2013, 9, 1326–1332, doi:10.3762/bjoc.9.149

• treatment of chiral enyne compounds. A good trans-selectivity was observed in the reaction. Results and Discussion We examined the cascade process using optically active enyne precursor 1a, which was prepared by a Michael/aldol domino reaction to chiral sulfinimines followed by thermal elimination and N

Synthesis of functionalized spiro[indoline-3,4’-pyridines] and spiro[indoline-3,4’-pyridinones] via one-pot four-component reactions

• Li-Juan Zhang,
• Qun Wu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2013, 9, 846–851, doi:10.3762/bjoc.9.97

• good yields by using this one-pot domino reaction procedure (Table 1). It can be seen that aniline bearing methoxy, methyl or chloro groups all reacted smoothly to give the expected spiro[indoline-3,4’-pyridines] with marginal effect. Benzylamine also afforded good yields of the spiro product. The

• the mechanism of this domino reaction, a plausible reaction course was proposed to account for the different products based on the published reactions containing methyl propiolate [20][21][22], which are illustrated in Scheme 1. The first reaction is the formation of the key intermediate β-enamino

• domino reaction. Synthesis of spiro[indoline-3,4’-pyridine] 1a–1p by domino reaction. Synthesis of spiro[indoline-3,4’-pyridines] 2a–2h and spiro[indoline-3,4’-pyridinone] 3a–3n via domino reaction. Supporting Information Supporting Information File 8: Experimental details and detailed spectroscopic

Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles

• Rajesh K. Arigela,
• Sudhir K. Sharma,
• Brijesh Kumar and
• Bijoy Kundu

Beilstein J. Org. Chem. 2013, 9, 401–405, doi:10.3762/bjoc.9.41

• methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields. Keywords: 2-alkynylindoles; azides; 1,3-dipolar cycloaddition; domino reaction

• intramolecular 1,3-dipolar cycloaddition pathway and in turn lead to the sequential formation of 7- or 5-membered diazepine and triazole rings in a single step. In this communication, we report a versatile microwave-assisted three component domino reaction to furnish annulated tetracyclic

• diminished (54–65%) isolated yields. Conclusion In conclusion, we have developed a simple and efficient three-component domino reaction for the synthesis of highly substituted indolodiazepinotriazoles in good yields under microwave conditions. The domino sequence comprising N-1 alkylation, ring opening of

Reactions of salicylaldehyde and enolates or their equivalents: versatile synthetic routes to chromane derivatives

• Ishmael B. Masesane and
• Zelalem Yibralign Desta

Beilstein J. Org. Chem. 2012, 8, 2166–2175, doi:10.3762/bjoc.8.244

• 60. However, the reaction suffered from very poor yields (15–21%). The reaction is thought to proceed through the condensation of aldehyde 60 and prolinol 61 to give a chiral iminium-ion intermediate. This intermediate then undergoes a domino reaction involving a Michael reaction with salicylaldehyde

Facile synthesis of functionalized tetrahydroquinolines via domino Povarov reactions of arylamines, methyl propiolate and aromatic aldehydes

• Jing Sun,
• Hong Gao,
• Qun Wu and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2012, 8, 1839–1843, doi:10.3762/bjoc.8.211

• Jing Sun Hong Gao Qun Wu Chao-Guo Yan College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China 10.3762/bjoc.8.211 Abstract In the presence of p-toluenesulfonic acid as catalyst the domino reaction of arylamines, methyl propiolates and aromatic aldehydes in ethanol

• proceeded smoothly to give polysubstituted 1,2,3,4-tetrahydroquinolines in moderate yields. The reaction is believed to involve the Povarov reaction of in situ generated β-enamino ester with the in situ formed aromatic imine. Keywords: β-enamino ester; domino reaction; electron-deficient alkyne; Povarov

• reaction; tetrahydroquinoline; Introduction The Diels–Alder reaction is recognized as a powerful reaction in synthetic strategies for the production of natural and unnatural polycarbocycles and polyheterocycles [1][2][3]. Therefore, the hetero-Diels–Alder reactions and domino reaction procedures have been

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• -arylhydroxylamines with 1,3-dicarbonyl compounds in situ) to give 3-carbonylated benzofuran derivatives 300 [153]. Trisubstituted isoxazoles 303 were obtained from alkynyl oxime ether 301 through a gold-catalyzed domino reaction involving cyclization and subsequent Claisen-type rearrangement [154]. The presence of

When gold can do what iodine cannot do: A critical comparison

• Sara Hummel and
• Stefan F. Kirsch

Beilstein J. Org. Chem. 2011, 7, 847–859, doi:10.3762/bjoc.7.97

• realizing a highly efficient domino reaction that creates two new stereogenic centers and three new bonds. Other heteroatoms have also been successfully employed as internal nucleophiles for the trapping of positive charges. In gold-catalyzed cyclizations, Kozmin and co-workers reported the

Rh-Catalyzed rearrangement of vinylcyclopropane to 1,3-diene units attached to N-heterocycles

• Franca M. Cordero,
• Carolina Vurchio,
• Stefano Cicchi,
• Armin de Meijere and
• Alberto Brandi

Beilstein J. Org. Chem. 2011, 7, 298–303, doi:10.3762/bjoc.7.39

• shift in the cyclopropanated 1,6-diradical intermediate, which in this case is probably facilitated by the enhanced mobility of the benzylic hydrogen and by the formation of the conjugationally stabilized imine 9 [11]. The 1,3-dipolar cycloaddition/thermal rearrangement domino reaction of BCP (2) with

Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide

• Nikola Cindro,
• Margareta Horvat,
• Kata Mlinarić-Majerski,
• Axel G. Griesbeck and
• Nikola Basarić

Beilstein J. Org. Chem. 2011, 7, 270–277, doi:10.3762/bjoc.7.36

• compounds [49], we turned our attention to adamantylphthalimides [50][51][52]. Recently, in cooperation with the group of Griesbeck we discovered a photoinduced domino reaction of adamantylphthalimide that involves two consecutive γ H-abstractions and leads to a complex methanoadamantane benzazepinone 2

• (Scheme 1) [51]. The mechanism of the photoinduced domino reaction was investigated and it was found that it probably takes place from a higher excited triplet state or the singlet state [52]. Herein, we report the synthesis and photochemistry of a phthalimide derivative of homoadamantane 5. The research

• optimization was performed by use of DFT B3LYP/6-31G. Photoinduced domino reaction of adamantylphthalimide. Synthesis of homoadamantylphthalimide 5. Products after irradiation of 5. Proposed mechanism for the photochemical transformation of 5. Supporting Information Supporting Information File 48: Supporting

Synthesis of (–)-Indolizidine 167B based on domino hydroformylation/cyclization reactions

• Giuditta Guazzelli,
• Raffaello Lazzaroni and
• Roberta Settambolo

Beilstein J. Org. Chem. 2008, 4, No. 2, doi:10.1186/1860-5397-4-2

• multi-step domino reaction sequences which are a very convenient approach to complex architectures in one simple, safe, environmentally acceptable and resource-effective operation [12][13][14]. The mechanistic as well as synthetic implications of the oxo reaction involving vinyl and allyl aromatic and

An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium- catalyzed multi- component domino reaction

• Dipak Prajapati and
• Mukut Gohain

Beilstein J. Org. Chem. 2006, 2, No. 11, doi:10.1186/1860-5397-2-11