On water: iodine-mediated direct construction of 1,3-benzothiazines from ortho-alkynylanilines by regioselective 6-exo-dig cyclization

Kapil Mohan Saini, Rakesh K. Saunthwal, Shiv Kumar, Akhilesh K. Verma*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)

Abstract

Herein, we report the 6-exo-dig ring closure of ortho-alkynylanilines with readily available aroyl isothiocyanate. An environmentally benign, metal- and base-free, iodine promoted cascade synthesis of highly functionalized (benzo[1,3]thiazin-2-yl)benzimidic acids has been accomplished via in situ generated ortho-alkynylthiourea. The established methodology employs the abundant chemical feedstock of ortho-alkynylanilines and aroyl isothiocyanates and could be applied in the late-stage synthesis of pharmaceutically active 1,3-benzothiazine containing molecules. Furthermore, the discovered protocol exclusively delivers bis (benzo[1,3]thiazin-2-yl)dibenzimidic acid products and preserves the iodo-olefin substitution pattern which can be exploited by further derivatization.

Original languageEnglish
Pages (from-to)2657-2662
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number10
Early online date7 Feb 2019
DOIs
Publication statusE-pub ahead of print - 7 Feb 2019

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