Reagent-Controlled One-Pot Assembly of Divergent Indolopyrido-Quinazolinones via Uninterrupted
Chada Raji Reddy1, Adla Vijender1, Ankita Kumari1
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India.
Abstract:
Herein, a novel synthesis of different indolopyrido-quinazolinones by the reaction of easily accessible 2-indolyl quinazolinone with propargylic alcohols has been developed. This [4 + 2] annulation proceeds through sequential acid-catalyzed C-propargylation and base-promoted aza-annulation by forming C-C and C-N bonds in a one-pot operation. Interestingly, the reagent-controlled regiodivergent annulations were observed leading to diversely fused N1-C2 or C2-N3 indolopyrido-quinazolinones. This approach demonstrates access to 7,8-substituted dehydrorutaecarpine alkaloids and their unique structural isomers.
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The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.


