Abstract
A novel, efficient and environmentally friendly approach has been developed for the synthesis of biologically important bis-heterocyclic oxazepine-quinazolinone derivatives. The structurally interesting compounds of high purity were synthesized by a one-pot three-component reaction of 2-(2-formylphenoxy) acetic acid and 2-aminobenzamide as bifunctional reagents and an isocyanide without using any catalyst, with excellent overall yields.
Highlights
To date, the development of new methods for the synthesis of heterocyclic compounds has been and remains a hot topic in organic chemistry, due to their importance in biologically active natural products and synthetic materials (Armstrong and Collins, 2010; Kaur et al, 2016)
The results show the reaction proceeded via the pathway B affording a new interesting class of oxazepine-quinazolinone 5 in high yields
We have successfully developed a one-pot threecomponent four-center reaction strategy leading to novel bisheterocyclic oxazepine-quinazolinones which are two important pharmacological and biological scaffolds, starting from simple and readily available inputs
Summary
The development of new methods for the synthesis of heterocyclic compounds has been and remains a hot topic in organic chemistry, due to their importance in biologically active natural products and synthetic materials (Armstrong and Collins, 2010; Kaur et al, 2016). Sintamil (Nagarajan et al, 1986) and loxapine (Liao et al, 1999) were reported, due to their antidepressant and potential clozapine-like properties, respectively (Figure 1) (Samet et al, 2005; Liu et al, 2011) Considering the structural characteristics of the benzoxazepine-3-ones, the existence of seven-membered heterocyclic ring system, fused aromatic group and the group –N–C(=O)–, similar to protein amide bond, it is reasonable to expect inherent physiological activities (Agirbas et al, 2011). As a part of our ongoing research program on the isocyanide-based MCRs (Shaabani et al, 2007, 2008a,b, 2009, 2011, 2014, 2016; Hajishaabanha and Shaabani, 2014), a novel strategy was designed to explore the Ugi one-pot three-component fourcenter reaction with two bifunctional starting materials, 2(2-formylphenoxy)acetic acid 1 and 2-aminobenzamide 2 for the synthesis of bis-heterocyclic oxazepine-benzodiazepine 4 (Scheme 1, cyclization path A) or oxazepine-quinazolinone 5 (Scheme 1, cyclization path B) derivatives.
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