The arene–alkene photocycloaddition

• Ursula Streit and
• Christian G. Bochet

Beilstein J. Org. Chem. 2011, 7, 525–542, doi:10.3762/bjoc.7.61

• the intramolecular photocycloaddition of a cinnamoylamide and a benzamide moiety (Scheme 32) [97]. This reaction is very efficient and leads to high yields of the bicyclo[2.2.2]octadiene derivative. In this example, the cinnamoylamide is sensitized by benzil to its triplet excited-state. The proposed

Approaches towards the synthesis of 5-aminopyrazoles

• Ranjana Aggarwal,
• Vinod Kumar,
• Rajiv Kumar and
• Shiv P. Singh

Beilstein J. Org. Chem. 2011, 7, 179–197, doi:10.3762/bjoc.7.25

• the starting material (Scheme 8). In this reaction, compound 25 was readily hydrolyzed to afford the β-ketonitrile derivative, i.e., 4-(1-cyano-2-oxoethyl)benzamide 26 which reacted efficiently with hydrazines to give the corresponding 5-aminopyrazoles 27. Subsequent cleavage from the resin afforded 5

• , imidazo[1,2-b]pyrazol-2-ones. Synthesis of 5-amino-3-(pyrrol-2-yl)pyrazole-4-carbonitrile. Synthesis of N-(1,3-diaryl-1H-pyrazol-5-yl)benzamide. Synthesis of 3,7-bis(arylazo)-6-methyl-2-phenyl-1H-imidazo[1,2-b]pyrazoles. Synthesis of 3,5-diaminopyrazole. Synthesis of 5-amino-4-cyanopyrazole and 5-amino-3

Self-assembly and semiconductivity of an oligothiophene supergelator

• Pampa Pratihar,
• Suhrit Ghosh,
• Vladimir Stepanenko,
• Sameer Patwardhan,
• Ferdinand C. Grozema,
• Laurens D. A. Siebbeles and
• Frank Würthner

Beilstein J. Org. Chem. 2010, 6, 1070–1078, doi:10.3762/bjoc.6.122

• (dodecyloxy)benzamide (6). Compound 4 (2.94 mmol) was dissolved in 5 mL dry CH2Cl2 and cooled in an ice-bath. To this cold solution, 4 mL triethylamine was added slowly. The resulting mixture was ice-cooled for an additional 10 minutes and then a solution of compound 5 in 10 mL dry CH2Cl2 was added dropwise

Fused bicyclic piperidines and dihydropyridines by dearomatising cyclisation of the enolates of nicotinyl-substituted esters and ketones

• Heloise Brice,
• Jonathan Clayden and
• Stuart D. Hamilton

Beilstein J. Org. Chem. 2010, 6, No. 22, doi:10.3762/bjoc.6.22

• and new reactivity from simple, readily made starting materials. We have used cyclisations of benzamide-stabilised carbanions, for example, to give bicyclic functionalised indolinones as intermediates in the synthesis of the neuroactive amino acids [22][23][24][25][26][27][28][29][30][31][32], while

Synthesis of methylenebisamides using CC- or DCMT- activated DMSO

• Qiang Wang,
• Lili Sun,
• Yu Jiang and
• Chunbao Li

Beilstein J. Org. Chem. 2008, 4, No. 51, doi:10.3762/bjoc.4.51

• drastic reaction conditions [19][22]. In this paper, we report the reaction of amides with DMSO activated by CC or 2,4-dichloro-6-methoxy[1,3,5]triazine (DCMT) [24]. Results and Discussion Initially, we chose CC as the activation reagent and benzamide as a model substrate to optimize the reaction

• amides: considerable amounts of by-products were formed, probably due to the greater nucleophilicity of the aliphatic amides. In order to improve the yield of aliphatic amides, less active DCMT was used as activating reagent instead of CC. We also optimized the reaction conditions using benzamide as a

• these experiments, a possible mechanism [6][23][25] is shown in Scheme 5. Intermediate 1 reacted with amides by two pathways. When the reaction of benzamide and CC-activated DMSO was carried out in chloroform, S,S-dimethyl-N-benzoylsulfilimine (4) was isolated as a major product, most probably formed by

The enantiospecific synthesis of (+)-monomorine I using a 5-endo- trig cyclisation strategy

• Malcolm B. Berry,
• Donald Craig,
• Philip S. Jones and
• Gareth J. Rowlands

Beilstein J. Org. Chem. 2007, 3, No. 39, doi:10.1186/1860-5397-3-39

• protecting groups. The full evolution of the 5-endo-trig cyclisation-based pyrrolidine methodology will be described in a future publication. Key to the successful synthesis of (+)-monomorine I was the use of the N-(benzoyl)aminosulfone 11 (Scheme 3). Benzamide 11 could be prepared from N-(diphenylphosphinyl

Synthesis of phosphorothioates using thiophosphate salts

• Babak Kaboudin and
• Fatemeh Farjadian

Beilstein J. Org. Chem. 2006, 2, No. 4, doi:10.1186/1860-5397-2-4

• chlorides. Reaction of ammonium O,O'-diethyl thiophosphate with benzoyl chloride, as a model compound, in acetonitrile gave benzamide as the major product (Scheme 5). Benzoyl chloride reacts with ammonia (from ammonium O,O'-diethyl thiophosphate) faster than anion O,O'-diethyl thiophosphate to give

• benzamide. All efforts for solving this problem failed and in all cases benzamide was obtained as the major product. We decided to replace this ammonium ion with a triethyl ammonium ion and then to study the reaction of new salt with benzoyl chloride. Triethylammonium O,O'-diethyl thiophosphate was obtained

EcoScale, a semi- quantitative tool to select an organic preparation based on economical and ecological parameters

• Koen Van Aken,
• Lucjan Strekowski and
• Luc Patiny

Beilstein J. Org. Chem. 2006, 2, No. 3, doi:10.1186/1860-5397-2-3

• benzoic acid [24] Synthesis of benzamide [25] Synthesis of benzamide using HMDS [26] The penalty points to calculate the EcoScale The penalty points for example 1 The penalty points for example 2 The penalty points for example 3 The penalty points for example 4

Total syntheses of oxygenated brazanquinones via regioselective homologous anionic Fries rearrangement of benzylic O-carbamates

• Glaucia Barbosa Candido Alves Slana,
• Mariângela Soares de Azevedo,
• Rosângela Sabattini Capella Lopes,
• Cláudio Cerqueira Lopes and
• Jari Nobrega Cardoso

Beilstein J. Org. Chem. 2006, 2, No. 1, doi:10.1186/1860-5397-2-1

• conjecture that, barring the competitive [1,2]–Wittig rearrangement, and one-pot route, 3 → 4 → 1, may be established in a direct manner without resort to DoM-derived benzamide intermediate, thereby establishing new carbonyl dianion equivalency 4 (see Scheme 1). We now report the versatility of this strategy