Anthracene coupled adenine for the selective sensing of copper ions

• Kumaresh Ghosh and
• Tanushree Sen

Beilstein J. Org. Chem. 2010, 6, No. 44, doi:10.3762/bjoc.6.44

• . First, 9-position of adenine was alkylated in the presence of NaH in dry DMF using 9-chloromethylanthracene, obtained from the reaction of 9-anthracenyl alcohol with thionyl chloride, to afford 2 [28] in 50% yield. In a similar manner, 9-butyladenine 3 was obtained from the reaction of adenine with n

Concise methods for the synthesis of chiral polyoxazolines and their application in asymmetric hydrosilylation

• Wei Jie Li,
• Zun Le Xu and
• Sheng Xiang Qiu

Beilstein J. Org. Chem. 2010, 6, No. 29, doi:10.3762/bjoc.6.29

• by cyclization to afford the target compounds. The methods require activating agents or cyclizing agents such as thionyl chloride, methanesulfonic chloride or PPh3 etc. [19][20][21], which result in more side reactions and low yields. Therefore, simpler and more efficient synthetic strategies are

• condensing agents such as thionyl chloride/NaOH, methanesulfonic chloride or PPh3 etc. to produce the desired compounds [19][20][21]. However, these methods are associated with side reactions and low yields. To address these issues, we have successfully developed facile procedures for the syntheses of

Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide – a tailor-made photoinitiator for dental adhesives

• Norbert Moszner,
• Iris Lamparth,
• Jörg Angermann,
• Urs Karl Fischer,
• Frank Zeuner,
• Thorsten Bock,
• Robert Liska and
• Volker Rheinberger

Beilstein J. Org. Chem. 2010, 6, No. 26, doi:10.3762/bjoc.6.26

• followed by recrystallization of the crude product from cyclohexane. In the second step, 1 was chlorinated with thionyl chloride in toluene as solvent by a procedure analogous to that described in the literature [16]. After distillation of the dark crude product, 3-{[2-[allyloxy)ethoxy]methyl}-2,4,6

• . The identity of compound 4 was established by an independent synthesis of the compound from 2-(allyloxy)ethanol and 3-(chloromethyl)-2,4,6-trimethylbenzoyl chloride 3, prepared by chlorination of 3-(chloromethyl)-2,4,6-trimethylbenzoic acid with thionyl chloride. In the third step, the

• ) and N,N-dimethylformamide (1.4 mL). Thionyl chloride (33.5 g, 0.282 mol) was added at room temperature. After 2 h, toluene was distilled off and a stream of nitrogen was bubbled through the crude product for 4 h before it was purified by vacuum distillation (130 °C, 0.05 mbar) to give 2 as a colorless

Synthesis and binding studies of two new macrocyclic receptors for the stereoselective recognition of dipeptides

• Ana Maria Castilla,
• M. Morgan Conn and
• Pablo Ballester

Beilstein J. Org. Chem. 2010, 6, No. 5, doi:10.3762/bjoc.6.5

• hydrochloride by treatment with thionyl chloride in methanol followed by acylation of the amino group with tert-butyl dicarbonate to yield Boc-I-Phe-OMe, 4a. Iodo-L-phenylalanine 6 was acylated under Schotten–Baumann conditions with benzyl chloroformate to obtain the N-protected amino acid Cbz-I-Phe. This

[3.3]Dithia-bridged cyclophanes featuring a thienothiophene ring: synthesis, structures and conformational analysis

• Sabir H. Mashraqui,
• Yogesh Sanghvikar,
• Shailesh Ghadhigaonkar,
• Sukeerthi Kumar,
• Auke Meetsma and
• Elise Trân Huu Dâu

Beilstein J. Org. Chem. 2009, 5, No. 74, doi:10.3762/bjoc.5.74

• in dry dichloromethane and freshly distilled thionyl chloride (1.0 ml, 13.6 mmol) was added dropwise at 5–10 °C. The reaction mixture was allowed to warm to room temperature over 5 h. The reaction mixture was then concentrated and the obtained brown solid was boiled with light petroleum ether. The

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

• Chloroaldehydes 1a,b are readily reduced under mild conditions by sodium borohydride to yield the alcohols 3a,b. Treatment of compounds 3a,b with thionyl chloride in dry benzene results in the formation of dichloro derivatives 4a,b, whilst the 3-bromomethyl derivatives 5a,b are obtained by refluxing 3a,b in

• benzene (6 mL) thionyl chloride (1.5 mL) was added dropwise at room temperature. The solution was stirred for 3 hours and concentrated in vacuo. Water was added and the solid product filtered off. Pure 4a,b was obtained by crystallization from hexane (95–98%). General procedure for the synthesis of

Dipyridodiazepinone derivatives; synthesis and anti HIV-1 activity

• Nisachon Khunnawutmanotham,
• Nitirat Chimnoi,
• Arunee Thitithanyanont,
• Patchreenart Saparpakorn,
• Kiattawee Choowongkomon,
• Pornpan Pungpo,
• Supa Hannongbua and
• Supanna Techasakul

Beilstein J. Org. Chem. 2009, 5, No. 36, doi:10.3762/bjoc.5.36

• produce aldehydes 21 in good yields. The reduction of 21 with NaBH4 produced alcohols 22, which were converted to the corresponding chlorides 23 through treatment with thionyl chloride in dichloromethane. The reaction of 23a with thiophenolate, 3-methoxythiophenolate, and 3-fluorothiophenolate in N,N

Mitomycins syntheses: a recent update

• Jean-Christophe Andrez

Beilstein J. Org. Chem. 2009, 5, No. 33, doi:10.3762/bjoc.5.33

• group and by deprotection of the ketal with acetic acid. The resultant diol was reacted with thionyl chloride and the corresponding sulfite 222 was opened with sodium azide; oxidation to the more reactive sulfate was not necessary. The final sequence involved deprotection of the acetate followed by

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

• synthesis of SBBC through which first the surface of silica gel was converted to silica chloride by means of reaction with thionyl chloride [27][28]. The silica chloride was heated with 4-hydroxybenzoic acid to form the silica-bound benzoic acid (SBBA). The SBBA was washed with acetone to remove excess 4

• -hydroxybenzoic acid. Finally, the silica-bound benzoyl chloride, SBBC, was obtained from the reaction of SBBA with thionyl chloride. The IR spectrum of SBBA revealed a band around 1660 cm−1 clearly indicative of C=O stretching vibration of the carboxyl groups while the absorbtion of C=O stretching vibration of

• dichloromethane and recovered by refluxing in thionyl chloride. Also, interesting to note is that under similar conditions and reaction times the treatment of 2-acylaminobenzoic acids with silica chloride 1 did not furnish the corresponding benzoxazinones. To investigate the recoverability of SBBC its reaction

Synthesis of crispine A analogues via an intramolecular Schmidt reaction

• Ajoy Kapat,
• Ponminor Senthil Kumar and
• Sundarababu Baskaran

Beilstein J. Org. Chem. 2007, 3, No. 49, doi:10.1186/1860-5397-3-49

• as a white crystalline solid. Diol 9 on bromination followed by nucleophilic displacement with NaCN furnished the desired dicyano compound 10. Treatment of dicyanide 10 with thionyl chloride in methanol gave the corresponding diester 11 as a colorless liquid in good yield. Compound 11 was then

Development of potential manufacturing routes for substituted thiophenes – Preparation of halogenated 2-thiophenecarboxylic acid derivatives as building blocks for a new family of 2,6-dihaloaryl 1,2,4-triazole insecticides

• John W. Hull Jr.,
• Duane R. Romer,
• David E. Podhorez,
• Mezzie L. Ash and
• Christine H. Brady

Beilstein J. Org. Chem. 2007, 3, No. 23, doi:10.1186/1860-5397-3-23

• ). Route selection studies carried out for approaches to 1 are summarized in Scheme 2. The key target was the bromo thiophene-2-carboxylic acid intermediate 19, which could be readily and cleanly converted to 1 by treatment with thionyl chloride. Scheme 2 shows three potential routes to 19 which were

• with CO2, 3,4,5-trichloro-2-thiophenecarboxylic acid 23 was isolated and dried prior to its conversion to 2 with thionyl chloride. Thus, 2 can be prepared in two chemical steps from the inexpensive chlorinated thiophene 22 using either lithiation or Grignard chemistry. [28] A comparison of some key

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• acid catalyst such as ytterbium triflate, revealed unsuccessful, only leading to recover the starting material. To overcome this difficulty, we turned to a more electrophilic sulfate moiety [36] (Scheme 3). Thus, treatment of the cis-diols 3 and 4 with thionyl chloride in the presence of triethylamine