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One-step construction of complex polyheterocycles via a sequential post-GBB cyclization/spiro ring expansion triggered by a [1,5]-hydride shift

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Abstract

An efficient tandem route to novel amino-indazolo[3′,2′:2,3]imidazo[1,5-c]quinazolin-6(5H)-ones has been explored. The reaction proceeds via a cascade involving an Ugi-variant Groebke–Blackburn–Bienayme (GBB) reaction that occurs through the in situ generation of a spirocyclic intermediate, which undergoes sequential ring opening via a [1,5]-hydride shift followed by an intramolecular nucleophilic reaction of the newly generated isocyanate to furnish complex polyheterocyclic frameworks. The main advantages of this protocol include short reaction time, excellent yield, easy work-up, operational simplicity and the absence of extraction and chromatographic purification steps.

Graphical abstract: One-step construction of complex polyheterocycles via a sequential post-GBB cyclization/spiro ring expansion triggered by a [1,5]-hydride shift

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Publication details

The article was received on 22 Jan 2018, accepted on 22 Mar 2018 and first published on 22 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00071A
Citation: Org. Chem. Front., 2018, Advance Article
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    One-step construction of complex polyheterocycles via a sequential post-GBB cyclization/spiro ring expansion triggered by a [1,5]-hydride shift

    S. G. Balwe and Y. T. Jeong, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00071A

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