β-Naphthol in Glycerol: A Versatile Pair for Efficient and Convenient Synthesis of Aminonaphthols, Naphtho-1,3-oxazines, and Benzoxanthenes

Subramaniapillai Selva Ganesan; Narendran Rajendran; Sankahr Ilathur Sundarakumar; Asaithampi Ganesan; Brindha Pemiah

doi:10.1055/s-0033-1338430

Synthesis, Table of Contents

Synthesis 2013; 45(11): 1564-1568
DOI: 10.1055/s-0033-1338430

paper

β-Naphthol in Glycerol: A Versatile Pair for Efficient and Convenient Synthesis of Aminonaphthols, Naphtho-1,3-oxazines, and Benzoxanthenes

Subramaniapillai Selva Ganesan*

^aSchool of Chemical and Biotechnology, SASTRA University, Thanjavur 613401, Tamil Nadu, India Fax: +91(4362)264120 Email: selva@biotech.sastra.edu

,

Narendran Rajendran

^bCARISM, SASTRA University, Thanjavur 613401, Tamil Nadu, India

,

Sankahr Ilathur Sundarakumar

^aSchool of Chemical and Biotechnology, SASTRA University, Thanjavur 613401, Tamil Nadu, India Fax: +91(4362)264120 Email: selva@biotech.sastra.edu

,

Asaithampi Ganesan

^aSchool of Chemical and Biotechnology, SASTRA University, Thanjavur 613401, Tamil Nadu, India Fax: +91(4362)264120 Email: selva@biotech.sastra.edu

,

Brindha Pemiah

^bCARISM, SASTRA University, Thanjavur 613401, Tamil Nadu, India

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Abstract

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Abstract

Three-component Betti reaction was carried out in the environmentally benign, inexpensive, non-toxic solvent glycerol. Even in the absence of a catalyst, the reaction went completion with an unprecedented high rate and the expected Betti bases were obtained in up to 91% yield. The reaction works well for representative cyclic, acyclic, aliphatic, and aromatic amines and aldehydes. A benzoxanthene was also prepared in 93% yield following the same methodology with 20 mol% methanesulfonic acid catalyst.

Key words

glycerol - Betti reaction - one-pot synthesis - naphtho-1,3-oxazine - benzoxanthenes

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References

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