A synthesis of spiroindolo[2, 1-b]quinazoline-6, 2'-pyrido[2, 1-b][1, 3]oxazines from tryptanthrins and Huisgen zwitterions. Issue 10 (19th May 2021)

• Record Type: Journal Article
• Authors: Yavari, Issa; Askarian-Amiri, Mohammad
• Is Part Of: Synthetic communications. Volume 51:Issue 10(2021)
• Page Start: 1602
• Page End: 1608
• Publication Date: 2021-05-19
• Subjects: 1, 4-Dipolar cycloaddition -- Huisgen zwitterion -- 1, 3-oxazines -- spiro compound -- tandem reaction; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2021.1899237
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: The Huisgen zwitterionic intermediates, generated in situ from N -heterocycles and acetylenic esters were intercepted by tryptanthrins to afford novel spiroindolo[2, 1- b ]quinazoline-6, 2'-pyrido[2, 1- b ][1, 3]oxazines in CH2 Cl2 at room temperature. Clear evidence for the structure of a derivative was obtained from single-crystal X-ray analyses. The most important feature of this reaction is the fact it forms two stereogenic centers, one of which is quaternary with remarkable diastereoselectivity. Graphical Abstract: