Diversity-oriented synthesis of dihydrobenzoxazepinones by coupling the Ugi multicomponent reaction with a Mitsunobu cyclization

• Lisa Moni,
• Luca Banfi,
• Andrea Basso,
• Alice Brambilla and
• Renata Riva

Beilstein J. Org. Chem. 2014, 10, 209–212, doi:10.3762/bjoc.10.16

• reaction of an ortho-(benzyloxy)benzylamine, glycolic acid, an isocyanide and an aldehyde, followed by an intramolecular Mitsunobu substitution was developed. The required ortho-(benzyloxy)benzylamines have been in situ generated from the corresponding azides, in turn prepared in high yields from salicylic

• because of interference of the phenol moiety, which can act as internal nucleophile. For these reasons we decided to use the O-benzylated benzylamines as starting materials for the U-4CR, postponing the hydrogenolytic removal of the protecting group after the condensation. Four different benzyl azides 2a

A general and facile one-pot process of isothiocyanates from amines under aqueous conditions

• Nan Sun,
• Bin Li,
• Jianping Shao,
• Weimin Mo,
• Baoxiang Hu,
• Zhenlu Shen and
• Xinquan Hu

Beilstein J. Org. Chem. 2012, 8, 61–70, doi:10.3762/bjoc.8.6

• time. This rate difference could be originated from the different basicities and their differences in water solubility. Once the dithiocarbamate was generated, the desulfurylation step using TCT proceeded smoothly for all amines. The branched alkylamines, cyclic alkylamines and benzylamines showed

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• failed with tosylamine and benzylcarbamate, whereas aryl-, alkyl- and benzylamines were used successfully in this reaction (Scheme 25). A three-component reaction involving in the first step a Sonogashira coupling of o-haloanilines 57 with terminal alkynes and leading to o-alkynylaniline intermediates 58

A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas

• Keith Smith,
• Gamal A. El-Hiti,
• Amany S. Hegazy and
• Benson Kariuki

Beilstein J. Org. Chem. 2011, 7, 1219–1227, doi:10.3762/bjoc.7.142

• procedures for the lithiation of various substituted benzylamines [69][70][71]. Similar subtleties over the site(s) of lithiation are also observed for these compounds. The site(s) of lithiation depend on the substituents at nitrogen, the nature and positions of substituents on the aryl ring and/or on 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

• -methoxybenzothiazines 10a,b, N-benzylamines 11a,b and sulfanylethanol derivatives 12a,b, respectively (Scheme 3). Conclusion In summary, we describe the preparation of novel benzo[e][2,1]thiazine derivatives capable of further modification. In particular β-hydroxymethylchlorides 3a,b, amines 7a,b and 4-chlorobenzo[e