On the functionalization of benzo[e][2,1]thiazine

• Kirill Popov,
• Tatyana Volovnenko and
• Julian Volovenko

Beilstein J. Org. Chem. 2009, 5, No. 42, doi:10.3762/bjoc.5.42

• shown to be quite versatile. Compounds 1 and 2 both contain 1,3-dielectrophilic fragments, which are C-4 carbon atoms of the benzothiazine ring and carbonyl group or nitrile function, respectively. Thus, further investigation of aldehydes 1 and nitriles 2 should provide new benzo[e][2,1]thiazine

The development and evaluation of a continuous flow process for the lipase- mediated oxidation of alkenes

• Charlotte Wiles,
• Marcus J. Hammond and
• Paul Watts

Beilstein J. Org. Chem. 2009, 5, No. 27, doi:10.3762/bjoc.5.27

• found widespread application in the conversion of nitriles to amides [32], aldehydes to acids [33], and sulfides to sulfones [34]. To enable comparison of the method developed here with batch investigations previously conducted, the oxidation of 1-methylcyclohexene (6) to 1-methylcyclohexene oxide (7

Synthesis of novel photochromic pyrans via palladium- mediated reactions

• Christoph Böttcher,
• Gehad Zeyat,
• Saleh A. Ahmed,
• Elisabeth Irran,
• Thorben Cordes,
• Cord Elsner,
• Wolfgang Zinth and
• Karola Rueck-Braun

Beilstein J. Org. Chem. 2009, 5, No. 25, doi:10.3762/bjoc.5.25

• rearrangement reactions [25]. Since nitriles are important intermediates in the synthesis of carboxylic acids and derivatives, and for the introduction of aminomethyl substituents, we started our studies with palladium-catalyzed cyanation reactions. The studies were then extended towards a Heck carbonylation in

• for the fine chemical industry, a variety of methods have been developed recently for the efficient cyanation of aryl halides under mild conditions. By applying electron-rich phosphanes and either Zn(CN)2 or K4[Fe(CN)6], the transformation of chlorides to nitriles was successfully achieved under

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

• ], hexamethylenetetramine [21] or activated DMSO [6], or by the reaction of nitriles with formaldehyde [22] or activated sulfoxides [23]. However, each method has certain limitations with regards to scope and reaction conditions, for example, longer reaction time [20], lower yield [6], purification problems [21][23] and

The role of an aromatic group in remote chiral induction during conjugate addition of α-sulfonylallylic carbanions to ethyl crotonate

• Shlomo Levinger,
• Ranjeet Nair and
• Alfred Hassner

Beilstein J. Org. Chem. 2008, 4, No. 32, doi:10.3762/bjoc.4.32

• acetophenones. Preparation of [(9-anthryl)alkyl]- and (mesitylalkyl)amines 6h and 6j from nitriles via imines 8. Preparation of α-sulfonylallylic donor precursors 1 according to Scheme 2. Remote chiral induction in the conjugate addition of lithiated α-sulfonylallyl anions of 1 to ethyl crotonate (2

Efficient 1,4-addition of α-substituted fluoro(phenylsulfonyl)methane derivatives to α,β-unsaturated compounds

• G. K. Surya Prakash,
• Xiaoming Zhao,
• Sujith Chacko,
• Fang Wang,
• Habiba Vaghoo and
• George A. Olah

Beilstein J. Org. Chem. 2008, 4, No. 17, doi:10.3762/bjoc.4.17

• nucleophile to a variety of α,β-unsaturated compounds has been achieved under mild conditions using either phosphines or potassium carbonate at room temperature. α-Substituted fluoro(phenylsulfonyl)methane easily undergoes Michael addition to α,β-unsaturated ketones, esters, nitriles, sulfones, as well as

• /DMF system was found to be very efficient both in terms of conversions as well as reaction times. The reactions were carried out at room temperature and the completion observed within 2 h. The reaction was found to be versatile for various α,β-unsaturated compounds such as ketones, esters, nitriles

• and sulfones (Table 3). In case of α,β-unsaturated aldehydes the reaction was found to be not clean and too many fluorine peaks appeared in the 19F NMR even when the reaction was carried out at low temperatures. On the other hand, α,β-unsaturated nitriles underwent a second Michael addition of the

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

• key step is the syn addition of the tin cuprate to the acetylene, which controls the cis stereochemistry required for cyclization. [23] Seven Membered Carbocycles The use of nitriles and imines as electrophiles in the silylcupration of allene provides new alternatives for carbocyclization. Recently

• , we showed that α,β-unsaturated nitriles undergo a double addition process when treated with the cuprate species resulting from addition of 1 to allene, giving ketones 44 containing both an allylsilane group and a vinylsilane moiety (Scheme 10). [24] Equilibration between species 2 and 45 as the

Cobalt(II) chloride catalyzed one-pot synthesis of α-aminonitriles

• Surya K. De

Beilstein J. Org. Chem. 2005, 1, No. 8, doi:10.1186/1860-5397-1-8

• (II) chloride- catalyzed synthesis of α-amino nitriles with potassium cyanide Supporting Information Supporting Information File 6: Experimental details.