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DFT Studied Hetero‐Diels–Alder Cycloaddition for the Domino Synthesis of Spiroheterocycles Fused to Benzothiazole and Chromene/Pyrimidine Rings in Aqueous Media
Author(s) -
Kumar Mahendra,
Arya Anand Kumar,
George Johnson,
Arya Kritika,
Pardasani R.T.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2964
Subject(s) - benzothiazole , chemistry , cycloaddition , thiazole , domino , pyrimidine , diels–alder reaction , aqueous solution , aqueous medium , cyclohexane , cascade reaction , combinatorial chemistry , organic chemistry , stereochemistry , catalysis
Structurally diverse spiroheterocycles; spiro[pyrimido[2,1‐ b ]benzothiazole‐3,3′‐chromene]‐2′,4′‐dione, spiro[pyrimido[2,1‐ b ]benzothiazole‐3,5′‐pyrimidine]‐2′,4′,6′‐trione, and spiro[pyrimido[2,1‐ b ]benz‐thiazole‐3,2′‐cyclohexane]‐1′,3′‐dione have been synthesized by an environmentally benign, efficient, and facile one‐pot pseudo‐four component reaction of 2‐aminobenzothiazoles with aromatic aldehydes and cyclic β‐diketones in aqueous medium. The process involves hetero‐Diels–Alder cycloaddition and provides facile access to spiroheterocycles fused with potentially interesting biologically active scaffolds. The configuration of hetero‐Diels–Alder cycloadduct has been ascertained through density functional theory calculations.