Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters

• Satish S. More,
• T. Krishna Mohan,
• Y. Sateesh Kumar,
• U. K. Syam Kumar and
• Navin B. Patel

Beilstein J. Org. Chem. 2011, 7, 831–838, doi:10.3762/bjoc.7.95

• -chloromethylene)malonates 19. The chloro alkenyl malonates 19 were synthesized in two steps from diethyl malonate and acid chlorides. The acylation of diethyl malonate was carried out with various acyl chlorides in the presence of anhydrous magnesium chloride and triethylamine, as per the reaction conditions

A new and facile synthetic approach to substituted 2-thioxoquinazolin-4-ones by the annulation of a pyrimidine derivative

• Nimalini D. Moirangthem and
• Warjeet S. Laitonjam

Beilstein J. Org. Chem. 2010, 6, 1056–1060, doi:10.3762/bjoc.6.120

• ], and with ketones or acid chlorides under acidic or basic conditions [15][16][17]. However, most of the methods involve multistep processes and time-consuming experimental procedures, and give poor yields or use toxic reagents. Moreover, very few methods are reported for the synthesis of 2

Chemical aminoacylation of tRNAs with fluorinated amino acids for in vitro protein mutagenesis

• Shijie Ye,
• Allison Ann Berger,
• Dominique Petzold,
• Oliver Reimann,
• Benjamin Matt and
• Beate Koksch

Beilstein J. Org. Chem. 2010, 6, No. 40, doi:10.3762/bjoc.6.40

• considerably the reactivity of both the amino and carboxylic groups; there is also a steric effect in this case. The amino group of α-(Tfm)Ala is generally protected by treatment with highly reactive mixed anhydrides or acid chlorides [28]. Thus, the N-(4-pentenoyl)-α-(Tfm)Ala was synthesized by means of 4

Ring-alkyl connecting group effect on mesogenic properties of p-carborane derivatives and their hydrocarbon analogues

• Aleksandra Jankowiak,
• Piotr Kaszynski,
• William R. Tilford,
• Kiminori Ohta,
• Adam Januszko,
• Takashi Nagamine and
• Yasuyuki Endo

Beilstein J. Org. Chem. 2009, 5, No. 83, doi:10.3762/bjoc.5.83

• homologues of 16A[6], diesters 16A[5] and 16A[7]. Results Synthesis Diesters 16[n] were prepared from diphenols 21 and appropriate carboxylic acid chlorides in the presence of a base as shown in Scheme 1. The requisite diphenols 21 were obtained in nearly quantitative yields by treating the corresponding

• the corresponding acid chlorides using PCl5 and then reacted with phenols in the presence of a base. The previously described method [2] for the preparation of esters of bicyclo[2.2.2]octane-1,4-dicarboxylic acid (22C) was unsuccessful and the desired esters 19C and 20C were obtained from the diacid

Saddle-shaped tetraphenylenes with peripheral gallic esters displaying columnar mesophases

• Eugen Wuckert,
• Constanze Hägele,
• Frank Giesselmann,
• Angelika Baro and
• Sabine Laschat

Beilstein J. Org. Chem. 2009, 5, No. 57, doi:10.3762/bjoc.5.57

• ][20][29][30][31], which was demethylated with boron tribromide in CH2Cl2 at −50 °C to room temp. followed by hydrolysis with MeOH (Scheme 1). Subsequent treatment with gallic acid chlorides in the presence of catalytic amounts of DMAP in pyridine/CH2Cl2 yielded after aqueous workup and chromatographic

Asymmetric reactions in continuous flow

• Xiao Yin Mak,
• Paola Laurino and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2009, 5, No. 19, doi:10.3762/bjoc.5.19

• also employed in a similar flow system for the asymmetric α-chlorination of acid chlorides (Scheme 7) [31][32]. This cinchona alkaloid derivative served the dual purpose of dehydrohalogenation and asymmetric induction, and was found to be reusable at least up to 100 times, after regeneration each time

• flow. Asymmetric synthesis of ß-lactams. α-Chlorination of acid chlorides in flow. Asymmetric Michael reaction in continuous flow. Enantioselective addition of Et2Zn to benzaldehyde using monolithic chiral amino alcohol. Continuous-flow hydrolytic dynamic kinetic resolution of epibromohydrin (32

Silica- bound benzoyl chloride mediated the solid- phase synthesis of 4H-3,1-benzoxazin- 4-ones

• Kurosh Rad-Moghadam and
• Somayeh Rouhi

Beilstein J. Org. Chem. 2009, 5, No. 13, doi:10.3762/bjoc.5.13

• ], reaction of anthranilic acid with acid chlorides [21], treatment of methyl N-aroylanthranilates or methyl 2-ureidobenzoates with concentrated sulfuric acid [22], rearrangement of o-nitrophenylacetic acid in boiling acetic anhydride [23], condensation of 2-azidobenzoic acid with aldehydes [24

• reagent and is prone to hydrolysis but in comparison with commonly used dehydrating acid chlorides such as acetyl chloride and benzoyl chloride which are more hygroscopic and difficult to handle, it has negligeable vapour pressure so can be used simply. In addition, SBBC is not lost to environment as it

New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

• Daisuke Sukeguchi,
• Surya Prakash Singh,
• Mamidi Ramesh Reddy,
• Hideyuki Yoshiyama,
• Rakesh A. Afre,
• Yasuhiko Hayashi,
• Hiroki Inukai,
• Tetsuo Soga,
• Shuichi Nakamura,
• Norio Shibata and
• Takeshi Toru

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

• heterojunction thin film. Synthesis of diarylmethanofullerene derivatives Diarylmethanofullerene derivatives were synthesized according to the method cited in the literature [26]. Synthetic routes are shown in Scheme 1. Generally, the Friedel–Crafts acylation of benzene derivatives 10–14 with acid chlorides 3–9

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

• methodology was limited by the finding that acylation of 3 (X = NDpp) could only be achieved with non-enolisable acid chlorides, rendering it unsuitable for the synthesis of (+)-monomorine I. Ultimately, no single protecting group was found to be suitable and it was necessary to exploit a combination of

Allylsilanes in the synthesis of three to seven membered rings: the silylcuprate strategy

• Asunción Barbero,
• Francisco J. Pulido and
• M. Carmen Sañudo

Beilstein J. Org. Chem. 2007, 3, No. 16, doi:10.1186/1860-5397-3-16

• -vinylcuprate species toward electrophiles increases their synthetic potential (Scheme 1). [7][8] A large number of electrophiles (alkyl and allyl halides, epoxides, ketones, α,β-unsaturated oxo compounds and acid chlorides, unsaturated nitriles and imines) have been successfully used in this reaction, leading

• oxocompounds provides an easy entry to the synthesis of oxoallylsilanes 3–8 which are useful synthons for cyclopentane annulations (Scheme 2). [7][9] Acid chlorides react with 2 affording divinyl ketones 9–10. Allylsilanes 3–8 carrying an electrophilic carbonyl moiety readily undergo intramolecular cyclization

• reaction between 2 and α,β-unsaturated acid chlorides provides an easy approach to silylated divinyl ketones 9–10 (Scheme 2), which are excellent precursors for silicon-directed Nazarov cyclizations. Acid catalysed electrocyclic closure (TFA, 0–20°C) allows the formation of exocyclic 2-methylenecyclopentan

Stereoselective α-fluoroamide and α-fluoro- γ-lactone synthesis by an asymmetric zwitterionic aza-Claisen rearrangement

• Kenny Tenza,
• Julian S. Northen,
• David O'Hagan and
• Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2005, 1, No. 13, doi:10.1186/1860-5397-1-13

• utilising α-fluorocarboxylic acid chlorides with N-allylmorpholine and N-allypyrrolidines. The reaction with N-allylmorpholine is efficient, however by using homochiral pyrrolidine auxiliaries, successful asymmetric reactions were achieved with (R)-N-allyl-2-(diphenylmethyl)pyrrolidine 15, but particularly