ItemArticle

Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines

Title
Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines
Creator
Putta V.P.R.K.; Vodnala N.; Gujjarappa R.; Tyagi U.; Garg A.; Gupta S.; Pujar P.P.; Malakar C.C.
Description
A reagent-controlled chemoselective process has been devised for the synthesis of 4H-1,3-benzoxazines and related biologically important heterocycles in high yields under mild conditions. These scaffolds could be efficiently constructed using two different chemoselective reactions that rely on the choice of reagents and reaction conditions. The treatment of various 2-amino-arylalkyl alcohols with isothiocyanates afforded thiourea intermediates, which were reacted in situ with molecular iodine in the presence of triethylamine to give 2-amino-4H-1,3-benzoxazines, whereas the corresponding 2-amino-4H-1,3-benzothiazines were obtained by the reaction of thiourea intermediates in the presence of T3P (a mild cyclodehydrating agent) and triethylamine as the base. The described protocol represents the first example for the synthesis of 4H-1,3-benzoxazines via the dehydrosulfurization method using molecular iodine as the reagent. Copyright 2019 American Chemical Society.
Source
Journal of Organic Chemistry, Vol-85, No. 2, pp. 380-396.
Date
2020-01-01
Publisher
American Chemical Society
Coverage
Putta V.P.R.K., Department of Medicinal Chemistry, Jubilant Biosys, Bangalore, Karnataka, 560022, India, Department of Chemistry, CHRIST, Deemed to Be University, Bangalore, 560029, India; Vodnala N., Department of Chemistry, National Institute of Technology Manipur, Imphal, Manipur, 795004, India; Gujjarappa R., Department of Chemistry, National Institute of Technology Manipur, Imphal, Manipur, 795004, India; Tyagi U., Department of Chemistry, National Institute of Technology Manipur, Imphal, Manipur, 795004, India; Garg A., Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Chunilal Bhawan, 168, Maniktala Main Road, Kolkata, 700054, India; Gupta S., Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research, Chunilal Bhawan, 168, Maniktala Main Road, Kolkata, 700054, India; Pujar P.P., Department of Chemistry, CHRIST, Deemed to Be University, Bangalore, 560029, India; Malakar C.C., Department of Chemistry, National Institute of Technology Manipur, Imphal, Manipur, 795004, India
Rights
Restricted Access
Relation
ISSN: 223263; PubMed ID: 31825620; CODEN: JOCEA
Format
Online
Language
English
Type
Article

Collection

Articles

Citation

Putta V.P.R.K.; Vodnala N.; Gujjarappa R.; Tyagi U.; Garg A.; Gupta S.; Pujar P.P.; Malakar C.C., “Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines,” CHRIST (Deemed To Be University) Institutional Repository, accessed February 28, 2025, https://archives.christuniversity.in/items/show/16311.

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