Synthetic Utility of the Vilsmeier–Haack Reagent in Organic Synthesis

Neena Neena; Vishwas Chaudhri; Fateh V. Singh; Hideyasu China; Toshifumi Dohi; Ravi Kumar

doi:10.1055/s-0042-1751421

Synlett, Table of Contents

Synlett 2023; 34(07): 777-792
DOI: 10.1055/s-0042-1751421

account

Chemical Synthesis and Catalysis in India

Synthetic Utility of the Vilsmeier–Haack Reagent in Organic Synthesis

Neena Neena

^aDepartment of Chemistry, Dyal Singh College, Karnal-132001, India

,

Vishwas Chaudhri

^bDepartment of Chemistry, J. C. Bose University of Science and Technology, YMCA, NH-2, Mathura Road, Faridabad-121006, India

,

Fateh V. Singh ∗

^cChemistry Division, School of Advanced Sciences, Vellore Institute of Technology (VIT)-Chennai, Vandalur-Kelambakkam Road, Chennai, Tamil Nadu 600127, India

,

Hideyasu China

^eGraduate School of Pharmaceutical Sciences, Ritsumeikan University, 1-1-1 Nojihigashi, Kusatsu, Shiga, 525-8577, Japan

,

Toshifumi Dohi∗

^dDepartment of Medical Bioscience, Nagahama Institute of Bio-Science and Technolog, 1266, Tamuracho, Nagahama-shi, Shiga 526-0829, Japan

,

Ravi Kumar∗

^aDepartment of Chemistry, Dyal Singh College, Karnal-132001, India

^bDepartment of Chemistry, J. C. Bose University of Science and Technology, YMCA, NH-2, Mathura Road, Faridabad-121006, India

› Author Affiliations

Abstract

All articles of this category

Abstract

The Vilsmeier–Haack reaction has historically been a topic of significant interest to organic chemists, and it continues to attract considerable attention. The reaction itself provides a facile route towards a large number of aromatic and heteroaromatic systems. The Vilsmeier–Haack reagent, generated from amides and halides, is found to be very important in organic synthesis. This account highlights recent developments in the synthetic utility of the Vilsmeier–Haack reagent.

1 Introduction

2 Formylation

3 Formylation and Chlorination

4 Formylation and Acetylation

5 Chlorination

6 ortho-Formylation

7 Miscellaneous

8 Conclusions

Key words

Vilsmeier–Haack reagent - formylation - chlorination - heterocycles

Full Text

References

References
1 Vilsmeier A. Chem.-Ztg. 1951; 75: 133
2 Bayer O. In Houben-Weyl Methods of Organic Chemistry, Vol. 7/1E. Georg Thieme Verlag; Stuttgart: 1954: 255
3 Brederec H, Gompper R, Vanchuh HG, Theiling G. Agnew. Chem. 1959; 71: 753
4 Eilingsfeld H, Seefelder M, Weidinger H. Angew. Chem. 1960; 72: 830
5 Minkin VI, Dorofeenko GN. Ospekhi Khim. 1960; 29: 1301 ; Chem. Abstr. 1961, 55, 12265h
6 Oda R, Yamamoto K. Kagaku 1960; 15: 384 ; Chem. Abstr. 1960, 54, 24325c
7 De Maheas MR. Bull. Soc. Chim. Fr. 1962; 30: 805
8 Hafner K, Häfner KH, König C, Kreuder M, Ploss G, Schulz G, Vöpel KH. Angew. Chem. 1963; 2: 123
9 Gore PH, Olah GA. Friedel–Crafts and Related Reactions, Vol. III. Wiley Interscience; New York: 1964: 64
10 Jutz C. Chem. Lab. Betrieb 1968; 19: 289
11 Ulrich H. The Chemistry of Imidoyl Halides . Plenum Press; New York: 1968
12 Kuehne ME. Enamines, Synthesis, Structure and Reactions . Cook AG. Marcel Dekker, Inc; New York: 1969
13 Seshadri S. J. Sci. Ind. Res. 1973; 32: 128
14 Jutz C. Advances in Organic Chemistry: Methods and Results . Taylor EC, Bochme H, Vieche HG. Wiley Interscience; New York: 1976
15 Meth-Cohn O, Tarnowski B. Cyclizations under Vilsmeier Conditions . In Advances in Heterocyclic Chemistry, Vol. 31. Katritzky AR. Academic Press; New York: 1982: 207
16 Simchen G. In Houben-Weyl Methods of Organic Chemistry, Vol. E3. Falbe J. Thieme; Stuttgart: 1983. S2
17 Marson CM. Tetrahedron 1992; 48: 3659
18 Meth-Cohn O, Stanforth SP. Comprehensive Organic Synthesis . Trost BM, Fleming I, Heathcock CH. Pergamon; Oxford: 1991: 777
19 Meth-Cohn O. Heterocycles 1993; 35: 539
20 Tasneem Tasneem. Synlett 2003; 138
21 Rajput AP, Girase PD. Int. J. Pharm. Chem. Biol. Sci. 2012; 3: 25
22 Weike S, Weng Y, Jiang L, Yang Y, Zhao L, Chen Z, Li Z, Li J. Org. Prep. Proced. Int. 2010; 42: 503
23 Inas S, Mahdi Zainab A, Sameaa J, Khammas Khammas, Majeed RA. Eurasian J. Biosci. 2020; 14: 973
24 Vilsmeier A, Haack A. Rep. Ger. Chem. Soc., Ser. A and B 1927; 60: 119
25 Filleux-Blanchard ML, Quemneur MT, Martin G. J. Chem. Commun. 1968; 83
26 Martin GJ, Poignant S, Filleux ML, Quemeneur MT. Tetrahedron Lett. 1970; 11: 5061
27 Abdelhamid IA, Shabban MR, Elwahy AH. M. Adv. Heterocycl. Chem. 2022; 136: 171
28 King WJ, Nord FF. J. Org. Chem. 1948; 13: 635
29 Clark BA. J, Parrick J, West PJ, Kelly AH. J. Chem. Soc. C 1970; 3: 498
30 Jutz C, Muller W. Chem. Rep. 1967; 100: 1536
31 Khan S, Shaheen M, Tabassum Z, Alam M. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2009; 48: 1183
32 Rajput AP, Rajput SS. Int. J. Pharm. Pharm. Sci. 2011; 3: 346
33 Mogilaiah K, Chandra AV, Srivani N, Praveena D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2013; 52: 698
34 Selvam TP, Kumar PV, Saravanan G, Prakash CR. J. Saudi Chem. Soc. 2014; 18: 1015
35 Ivonin SP, Kurpil BB, Rusanov EB, Grygorenko OO, Volochnyuk DM. Tetrahedron Lett. 2014; 55: 2187
36 Jupudi S, Talari S, Karunakaram D, Govindarajan R. Int. J. Res. Pharm. Chem. 2013; 3: 213
37 Subhashini NJ. P, Reddy ChB, Kumar PA, Lingaiah B. J. Appl. Chem. 2015; 4: 323
38 Popov A, Kobelevskaya VA, Larina LI, Rozentsveig IB. ARKIVOC 2019; (vi): 1
39 Meesala R, Nagarajan R. Tetrahedron Lett. 2006; 47: 7557
40 Shamsuzzaman Shamsuzzaman, Khanam H, Mashrai A, Siddiqui N. Tetrahedron Lett. 2013; 54: 874
41 Damodiran M, Panneer Selvam N, Perumal PT. Tetrahedron Lett. 2009; 50: 5474
42 Aneesa KC, Rajanna Y, Kumar A, Arifuddin M. Org. Chem. Int. 2012, 289023.
43 Mphahlele MJ, Mmonwa MM. Org. Biomol. Chem. 2019; 17: 2204
44 Roohi L, Afghan A, Baradarani MM. Curr. Chem. Lett. 2013; 2: 187
45 Khezri M, Afghan A, Roohi L, Baradarani M. Org. Chem. Res. 2016; 2: 120
46 Gao W, Jiang Y, Li Y, Li F, Yan Y. Chin. J. Chem. 2012; 30: 822
47 Alegaon SG, Alagawadi KR. Eur. J. Chem. 2011; 2: 94
48 Mikhaleva AI, Ivanov AV, Skital’tseva EV, Ushakov IA, Vasil’tsov AM, Trofimov BA. Synthesis 2009; 587
49 Hartmann H. ARKIVOC 2012; (iii): 356
50 Kantlehner W. Eur. J. Org. Chem. 2003; 2530 ; and references cited therein
51 Nasrullaev AO, Turdibaev ZE, Elmuradov BZ, Yili A, Aisa HA, Shakhidoyatov KM. Chem. Nat. Compd. 2012; 48: 638
52 Ortikov IS, Turdibaev ZÉ, Islamova ZI, Élmuradov BZ, Abdurazakov AS, Bektemirov AM, Osipova SO, Khushbaktova ZA, Syrov VN, Shakhidoyatov KM. Pharm. Chem. J. 2017; 51: 456
53 Loudet A, Burgess K. Chem. Rev. 2007; 107: 4891
54 Jiao L, Yu C, Li J, Wang Z, Wu M, Hao E. J. Org. Chem. 2009; 74: 7525
55 Ali HI, Ashida N, Nagamatsua T. Bioorg. Med. Chem. 2007; 15: 6336
56 Zhang Z, Kumar RK, Li G, Wu D, Bi X. Org. Lett. 2015; 17: 6190
57 Anabha ER, Asokan CV. Synthesis 2006; 151
58 Barman G, Ray JK. Tetrahedron Lett. 2010; 51: 297
59 Bala R, Devi V, Singh P, Kaur N, Kaur P, Kumar A, Yadav AN, Singh K. Lett. Org. Chem. 2019; 16: 194
60 Shaffer AR, Schmidt JA. Chem. Eur. J. 2009; 15: 2662
61 Ashok D, Lakshmi BV, Ganesh A, Ravi S, Adam S, Murthy SD. S. Russ. J. Gen. Chem. 2014; 84: 2234
62 Makhanya TR, Pitchai P, Gengan RM, Mohan PS. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2016; 55: 517
63 Tekale AS, Shaikh S. Int. J. Chem. Stud. 2017; 5: 1
64 Mahalingam M, Mohan PS, Gayathri K, Gomathi R, Subhapriya P. J. Chem. Sci. 2013; 125: 1015
65 Ruiz E, Rodríguez H, Coro J, Niebla V, Rodríguez A, Martínez-Alvarez R, Novoa de Armas H, Suárez M, Martín N. Ultrason. Sonochem. 2012; 19: 221
66 Ba LA, Kirsch G, Castello J. ARKIVOC 2007; (x): 374
67 Tang XY, Shi M. J. Org. Chem. 2008; 73: 8317
68 Kale M, Mene D. Int. J. Pharm. Bio. Sci. 2013; 4: 503
69 Aghera VK, Patel JP, Parsania PH. ARKIVOC 2008; (xii): 195
70 Chornous VA, Bratenko MK, Vovk MV. Russ. J. Org. Chem. 2009; 45: 1210
71 Zhang Z, Xue C, Liu X, Zhang Q, Liu Q. Tetrahedron 2011; 67: 7081
72 Mohammed T, Khan AA, Iqbal SM. S, Begum T. Adv. Mater. Lett. 2020; 11: 20021476
73 Liu Q, Che G, Yu H, Liu Y, Zhang J, Zhang Q, Dong D. J. Org. Chem. 2003; 68: 9148
74 Liu Y, Zheng H, Xu D, Xu Z, Zhang Y. Org. Prep. Proced. Int. 2007; 39: 190
75 Li J, Huo H, Guo R, Liu B, Li L, Dan W, Xiao X, Zhang J, Shi B. Eur. J. Med. Chem. 2017; 130: 1
76 Srivastava V, Negi AS, Kumar JK, Gupta MM. Steroids 2006; 71: 632
77 Kotlyar V, Shahar L, Lellouche JP. Mol. Diversity 2006; 10: 255
78 Sathiyamoorthy S, Pitchai P, Jemima D, Gengan RM. Res. Rev. J. Chem. 2018; 7: 45
79 Prakash O, Chaudhri V, Kinger M. Synth. Commun. 2005; 35: 2819
80 Rajanna KC, Venkanna P, Kumar MS, Ramgopal S. Int. J. Org. Chem. 2012; 2: 336
81 Rajanna KC, Kumar MS, Venkanna P, Ramgopal S, Venkateswarlu M. Int. J. Org. Chem. 2011; 1: 250
82 McCallum T, Barriault L. J. Org. Chem. 2015; 80: 2874
83 Kimura Y, Matsuura D. Int. J. Org. Chem. 2013; 3: 1
84 Chakradhar A, Roopa R, Rajanna KC, Saiprakash PK. Synth. Commun. 2009; 39: 1817
85 Ushijima S, Togo H. Synlett 2010; 1067
86 Ushijima S, Moriyama K, Togo H. Tetrahedron 2002; 68: 4588