Highly Selective Approach to α-Iodoketones from Aminoalkynols with Iodine Monochloride

Vijay V. Rao; Nedaossadat Mirzadeh; Suresh Bhargava; Pravin R. Likhar

doi:10.1055/s-0036-1590897

Synthesis, Table of Contents

Synthesis 2017; 49(24): 5380-5386
DOI: 10.1055/s-0036-1590897

paper

Highly Selective Approach to α-Iodoketones from Aminoalkynols with Iodine Monochloride

Vijay V. Rao

^aCenter for Advanced Materials and Industrial Chemistry, School of Applied Sciences, RMIT University, 124 LaTrobe Street, Melbourne VIC 3000, Australia Email: suresh.bhargava@rmit.edu.au

^bIICT-RMIT Joint Research Center, CSIR-IICT, Uppal Road, Tarnaka, Hyderabad 500007, India

,

Nedaossadat Mirzadeh

^aCenter for Advanced Materials and Industrial Chemistry, School of Applied Sciences, RMIT University, 124 LaTrobe Street, Melbourne VIC 3000, Australia Email: suresh.bhargava@rmit.edu.au

,

Suresh Bhargava*

^aCenter for Advanced Materials and Industrial Chemistry, School of Applied Sciences, RMIT University, 124 LaTrobe Street, Melbourne VIC 3000, Australia Email: suresh.bhargava@rmit.edu.au

,

Pravin R. Likhar*

^cOrganometallic Gp., I & P C Division, CSIR-IICT, Uppal Road, Tarnaka, Hyderabad 500007, India Email: plikhar@iict.res.in

› Author Affiliations

Abstract

All articles of this category

Abstract

A protocol has been developed to achieve selective and direct synthesis of α-iodoketones under mild condition, from the reaction of aminoalkynols with iodine monochloride. The scope of the reaction was investigated using various aminoalkynols with iodine monochloride and the corresponding α-iodoketones were obtained selectively without forming iodocyclized and/or addition products.

Key words

iodine monochloride - regioselective - iodonium activation - α-iodoketones - iodocyclization

Full Text

References

References

1a Gribble GW. Chem. Soc. Rev. 1999; 28: 335
1b Gribble GW. Heterocycles 2011; 84: 157

2a De Kimpe N. Verhé R. In α-Haloketones, α-Haloaldehydes and α-Haloimines. Wiley; Chichester: 1988
2b Erian AW. Sherif SM. Gaber HM. Molecules 2003; 8: 793

3a Barluenga J. Marco-Arias M. González-Bobes F. Ballesteros A. González JM. Chem. Commun. 2004; 9: 2616
3b Marri MR. Macharla AK. Peraka S. Nama N. Tetrahedron Lett. 2011; 52: 6554
3c Yusubov MS. Yusubova RY. Funk TV. Chi KW. Kirschning A. Zhdankin VV. Synthesis 2010; 3681
3d Stavber G. Iskra J. Zupan M. Stavber S. Adv. Synth. Catal. 2008; 350: 2921
3e Yang D. Yan YL. Lui B. J. Org. Chem. 2002; 67: 7429

4a Vankar YD. Kumaravel G. Tetrahedron Lett. 1984; 25: 233
4b Rosenkranz G. Mancera O. Gatica J. Djerassi C. J. Am. Chem. Soc. 1950; 72: 4077

5a Moorthy JN. Senapati K. Singhal N. Tetrahedron Lett. 2009; 50: 2493
5b Morton HE. Leanna MR. Tetrahedron Lett. 1993; 34: 4481
5c Yadav JS. Subba Reddy BV. Singh AP. Basak AK. Tetrahedron Lett. 2008; 49: 5880
5d Cardillo G. Shimizu M. J. Org. Chem. 1977; 42: 4268
5e Nakayama H. Itoh A. Tetrahedron Lett. 2007; 48: 1131

6a Chen Z. Jiang H. Li Y. Qi C. Chem. Commun. 2010; 46: 8049
6b Zou H. Jiang J. Yi N. Fu W. Deng W. Xiang J. Chin. J. Chem. 2016; 34: 1251
6c Xie L. Wu Y. Yi W. Zhu L. Xiang J. He W. J. Org. Chem. 2013; 78: 9190

7 Karkhelikar MV. Jha RR. Sridhar B. Likhar PR. Verma AK. Chem. Commun. 2014; 50: 8526
8 Vijay V. Karkhelikar MV. Sridhar B. Mirzadeh N. Bhargava S. Likhar PR. Org. Biomol. Chem. 2016; 14: 288
9 CCDC number 1554465 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

10a Bellina F. Colzi F. Mannina L. Rossi R. Viel S. J. Org. Chem. 2003; 68: 10175
10b Godoi B. Schumacher RF. Zeni G. Chem. Rev. 2011; 111: 2937

11a Mauger E. Berliner E. J. Am. Chem. Soc. 1972; 94: 194
11b Rossi R. Carpita A. Bellina F. Stabile P. Mannina L. Tetrahedron 2003; 59: 2067

12a Han J.-S. Chen S.-Q. Zhong P. Zhang X.-H. Synth. Commun. 2014; 44: 3148
12b Batistatos M. Fousteris MA. Nikolaropoulos SS. Le Bras J. Muzart J. Lett. Org. Chem. 2010; 7: 440
12c Fousteris M. Chevrin C. Le Bras J. Muzart J. Green Chem. 2006; 8: 522

Supplementary Material

Supporting Information