Synthesis 2020; 52(05): 769-774
DOI: 10.1055/s-0039-1690755
paper
© Georg Thieme Verlag Stuttgart · New York

Practical Synthesis of 1,2,3,4-Tetrahydroisoquinoline-1-phosphonic and -1-phosphinic Acids through Kabachnik–Fields and Aza-Pudovik Reaction

Jesús Tadeo Hernández-Moreno
a  Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico   Email: palacios@uaem.mx
,
Ivan Romero-Estudillo
a  Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico   Email: palacios@uaem.mx
b  CONACyT-Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico
,
Carlos Cativiela
c  Departamento de Química Orgánica, Universidad de Zaragoza-CSIC, ISQCH, Zaragoza 50009, Spain
,
a  Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Morelos 62209, Mexico   Email: palacios@uaem.mx
› Author Affiliations
The authors thank the Consejo Nacional de Ciencia y Tecnología (CONACyT) for financial support through projects 286614, 807, and Cátedra contract 942, and Gobierno de Aragón-FEDER (Grupo Aminoácidos y Péptidos E19_17R; FEDER 2014-2020 ‘Construyendo Europa desde Aragón’). J.T.H.-M. also wishes to thank CONACyT for Graduate Scholarship 335029.
Further Information

Publication History

Received: 20 October 2019

Accepted after revision: 07 November 2019

Publication Date:
26 November 2019 (online)


Abstract

We report here an alternative and practical method for the preparation of 1,2,3,4-tetrahydroisoquinoline-1-phosphonic acid and the first synthesis of 1,2,3,4-tetrahydroisoquinoline-1-H-phosphinic and 1,2,3,4-tetrahydroisoquinoline-1-phenylphosphinic acids through Kabachnik–Fields and aza-Pudovik reaction. This methodology does not require any metallic catalyst and proceeds under mild reaction conditions.

Supporting Information

 
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