Synthesis of Masked Vicinal
Amino Aldehydes of Pyrrolizine and Pyrrolo [1,2-c]thiazole Series

Anton V. Tverdokhlebov; Alexander V. Denisenko; Andrey A. Tolmachev; Yulian M. Volovenko; Svetlana V. Shishkina; Oleg V. Shishkin

doi:10.1055/s-0028-1088029

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Synthesis 2009(8): 1265-1270
DOI: 10.1055/s-0028-1088029

PAPER

Synthesis of Masked Vicinal Amino Aldehydes of Pyrrolizine and Pyrrolo [1,2-c]thiazole Series

Anton V. Tverdokhlebov*^a, Alexander V. Denisenko^b, Andrey A. Tolmachev^a,b, Yulian M. Volovenko^b, Svetlana V. Shishkina^c, Oleg V. Shishkin^c
^a Enamine Ltd., Alexandra Matrosova str. 23, 01103, Kiev, Ukraine
Fax: +38(044)5373253; e-Mail: atver@univ.kiev.ua;
^b Kiev National Taras Shevchenko University, Volodimirska str. 62, 01033, Kiev, Ukraine
^c STC ‘Institute for Single Crystals’, NAS of Ukraine, 60 Lenina ave., 61001, Kharkiv, Ukraine

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Publikationsverlauf

Received 29 September 2008
Publikationsdatum:
25. März 2009 (online)

Abstract
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Abstract

Acylation of (1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-ylidene)acetonitrile with mixed anhydrides of N-Boc proline and 4-thiazolidinecarboxylic acid was found to proceed at the exocyclic carbon atom yielding the corresponding C-acyl derivatives. Removal of the protecting group with equimolar amount of hydrochloric acid effected simultaneous cyclization affording 2-(3-amino-5,6,7,7a-tetrahydro-1-oxo-1H-pyrrolizin-2-yl)- and 2-(5-amino-7,7a-dihydro-7-oxo-1H,3H-pyrrolo[1,2-c]thiazol-6-yl)-1,3-dimethylbenzimidazolium chlorides. Reduction of the prepared salts with sodium borohydride resulted in 3-amino-2-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one and 5-amino-6-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-1,7a-dihydro-3H,7H-pyrrolo[1,2-c]thiazol-7-one, respectively. These compounds were shown to be masked aldehydes. Their reactions with phenylhydrazine and hydroxylamine yielded corresponding hydrazones and oximes, whereas condensation with malononitrile furnished 2-amino-5a,6,7,8-tetrahydro-5-oxo-5H-pyrido[3,2-b]pyrrolizine-3-carbonitrile and 2-amino-5a,6-dihydro-5H,8H-thiazolo[3′,4′:1,5]pyrrolo[2,3-b]pyridine-3-carbonitrile.

Key words

acylations - amino aldehydes - heterocycles - nitriles - reduction

References

1 For a review, see: Caluwe P. Tetrahedron 1980, 36: 2359

Crossref Google Scholar
2 Eger K. Pfahl JG. Folkers G. Roth HJ. J. Heterocycl. Chem. 1987, 24: 425

Crossref Google Scholar
3a Snider BB. Duvall JR. Sattler I. Huang X. Tetrahedron Lett. 2004, 45: 6725

Google Scholar
3b Snider BB. Duvall JR. Org. Lett. 2005, 7: 4519

Google Scholar
3c Duvall JR. Wu F. Snider BB. J. Org. Chem. 2006, 71: 8579

Google Scholar
4a Volovenko YuM. Shokol TV. Babichev FS. Dopov. Akad. Nauk Ukr. RSR, Ser. B. 1986, 2: 35 ; Chem. Abstr. 1987, 107, 163331

Google Scholar
4b Volovenko YuM. Chem. Heterocycl. Compd. (Engl. Transl.) 1997, 33: 854 ; Khim. Geterotsikl. Soedin. 1997, 975

Google Scholar
4c Hartke K. Radau S. Liebigs Ann. Chem. 1974, 2110

Google Scholar
4d Fares V. Flamini A. Poli N. J. Am. Chem. Soc. 1995, 117: 11580

Google Scholar
4e Bonamico M. Fares V. Flamini A. Imperatori P. Poli N. Angew. Chem., Int. Ed. Engl. 1989, 28: 1049

Google Scholar
4f Fares V. Flamini A. Poli N. J. Chem. Res., Synop. 1995, 228

Google Scholar
4g Bonamico M. Fares V. Flamini A. Giuliani AM. Imperatori P. J. Chem. Soc., Perkin Trans. 2 1988, 1447

Google Scholar
4h Collange E. Flamini A. Poli R. J. Phys. Chem. 2002, A106: 200

Google Scholar
4i Flamini A. Fares V. Capobianchi A. Valentini V. J. Chem. Soc., Perkin Trans. 1 2001, 3069

Google Scholar
5a Yang Z. Zhang S. J. Indian Chem. Soc. 2002, 79: 698

Google Scholar
5b Sun G. Yang Z. Zhang S. J. Indian Chem. Soc. 2003, 80: 851

Google Scholar
6a Varlamov AV. Borisova TN. Bonifas N. Chernyshev AI. Alexandrov GG. Voskresensky LG. Chem. Heterocycl. Compd. (Engl. Transl.) 2004, 40: 166 ; Khim. Geterotsikl. Soedin. 2004, 201

Google Scholar
6b Clare BW. Ferro V. Skeleton BW. Stick RV. White AH. Aust. J. Chem. 1993, 46: 805

Google Scholar
6c Abbiati G. Casoni A. Canevari V. Nava D. Rossi E. Org. Lett. 2006, 8: 4839

Google Scholar
6d Hamersma JAM. Nossin PMM. Speckamp WN. Tetrahedron 1985, 41: 1999

Google Scholar
6e Dannhardt G. Lehr M. Arch. Pharm. (Weinheim, Ger.) 1988, 321: 545

Google Scholar
7a Craig JC. Ekwuribe NN. Fu CC. Walker KAM. Synthesis 1981, 303

Google Scholar
7b Ramos JM. Tarazi M. Wuest JD. J. Org. Chem. 1987, 52: 5437

Google Scholar
7c Katritzky AR. Aslan DC. Oniciu DC. Tetrahedron: Asymmetry 1998, 2245

Google Scholar
7d Lee I.-SH. Jeoung EH. Kreevoy MM. J. Am. Chem. Soc. 1997, 119: 2722

Google Scholar
7e Lee I.-SH. Jeoung EH. J. Org. Chem. 1998, 63: 7275

Google Scholar
8 Tverdokhlebov AV. Denisenko AV. Tolmachev AA. Volovenko YuM. Synthesis 2007, 1811

Artikel in Thieme Connect Google Scholar
9a Rudnev MI. Kurbatov VP. Chub NK. Osipov OA. J. Gen. Chem. USSR (Engl. Transl.) 1988, 58: 2077 ; Zh. Obshch. Khim. 1988, 58, 2334

Google Scholar
9b Zakhs ER. Ponyaev AI. Subbotina MA. El’tsov AV. Russ. J. Gen. Chem. (Engl. Transl.) 2001, 71: 1076 ; Zh. Obshch. Khim. 2001, 71, 1142

Google Scholar
9c Zakhs ER. Subbotina MA. El’tsov AV. J. Org. Chem. USSR (Engl. Transl.) 1979, 15: 178 ; Zh. Org. Khim. 1979, 15, 200

Google Scholar
10a Gavai AV. Vaz RJ. Mikkilineni AM. Roberge JY. Liu Y. Lawrence RM. Corte JR. Yang W. Bednarz M. Dickson JK. Ma Z. Seethala R. Feyen JHM. Bioorg. Med. Chem. Lett. 2005, 15: 5478

Google Scholar
10b Bures F. Kulhanek J. Tetrahedron: Asymmetry 2005, 16: 1347

Google Scholar
10c Bernard E. Vanderesso R. Tetrahedron Lett. 2004, 45: 8603

Google Scholar
10d Vasanthakumar G.-R. Patil BS. Suresh Babu VV. J. Chem. Soc., Perkin Trans. 1 2002, 2087

Google Scholar
10e Lakeev SN. Mullagalin IZ. Galin FZ. Majdanova IO. Abdullin MF. Russ. Chem. Bull. 2002, 51: 2230 ; Izv. Akad. Nauk Ser. Khim. 2002, 2071

Google Scholar
10f Wallen EAA. Christiaans JAM. Saario SM. Forsberg MM. Venäläinen JI. Paso HM. Männistö PT. Gynther J. Bioorg. Med. Chem. 2002, 10: 2199

Google Scholar
10g Harrison JR. O’Brien P. Porter DW. Smith NM. J. Chem. Soc., Perkin Trans. 1 1999, 3623

Google Scholar
10h Plucinska K. Liberek B. Tetrahedron 1987, 43: 3509

Google Scholar
10i Fujimoto K. Iwano Y. Hirai K. Sugawara S. Chem. Pharm. Bull. 1986, 34: 999

Google Scholar
11a Wada CK. Holms JH. Curtin ML. Dai Y. Florjancic AS. Garland RB. Guo Y. Heyman HR. Stacey JR. Steinman DH. Albert DH. Bouska JJ. Elmore IN. Goodfellow CL. Marcotte PA. Tapang P. Morgan DW. Michaelides MR. Davidsen SK. J. Med. Chem. 2002, 45: 219

Google Scholar
11b Koskinen AMP. Kallatsa OA. Tetrahedron 2003, 59: 6947

Google Scholar
11c Verbicky CA. Zercher CK. J. Org. Chem. 2000, 65: 5615

Google Scholar
11d Yuste F. Ortiz B. Carrasco A. Peralta M. Quintero L. Sanchez-Obregon R. Walls F. Garcia Ruano JL. Tetrahedron: Asymmetry 2000, 11: 3079

Google Scholar
11e Wittenberger SJ. J. Org. Chem. 1996, 61: 356

Google Scholar
12a Bal G. Van der Veken P. Antonov D. Lambeir A.-M. Grellier P. Croft SL. Augustyns A. Halmers A. Bioorg. Med Chem. Lett. 2003, 13: 2875

Google Scholar
12b Hoffman RV. Tao J. J. Org. Chem. 1999, 64: 126

Google Scholar
13a Chen P. Cheng PTN. Spergel SH. Zahler R. Wang X. Thottathil J. Barrish JC. Polniaszek RP. Tetrahedron Lett. 1997, 38: 3175

Google Scholar
13b De Luca L. Giacomelli G. Porcheddu A. Org. Lett. 2001, 3: 1519

Google Scholar
13c Heathcock CH. von Geldern TW. Heterocycles 1987, 25: 75

Google Scholar
13d Elliott RL. Kopecka H. Lin N.-H. He Y. Garvey DS. Synthesis 1995, 772

Google Scholar
14a De Luca L. Giacomelli G. Taddei M. J. Org. Chem. 2001, 66: 2534

Google Scholar
14b Knight JG. Ley SV. Tetrahedron Lett. 1991, 32: 7119

Google Scholar
15a Overman LE. Lesuisse D. Tetrahedron Lett. 1985, 26: 4167

Google Scholar
15b Evans DA. Nelson JV. Vogel E. Taber TR. J. Am. Chem. Soc. 1981, 103: 3099

Google Scholar
15c Goldstein SW. Overman LE. Rabinowitz MH. J. Org. Chem. 1992, 57: 1179

Google Scholar
16a Aitken RA. Karodia N. Massil T. Young RJ. J. Chem. Soc., Perkin Trans. 1 2002, 533

Google Scholar
16b Aitken RA. Karodia N. J. Chem. Soc., Chem. Commun. 1996, 2079

Google Scholar
18a Nomura Y. Bando T. Takeuchi Y. Tomoda S. Bull. Chem. Soc. Jpn. 1984, 57: 1271

Google Scholar
18b Laduree D. Robba M. Heterocycles 1984, 22: 303

Google Scholar
19a Harris BD. Bhat KL. Joullie M. Heterocycles 1986, 24: 1045

Google Scholar
19b Swarbrick ME. Gosselin F. Lubell WD. J. Org. Chem. 1999, 64: 1993

Google Scholar
19c Oiry J. Pue JY. Fatome M. Sentenac-Roumanou H. Lion C. Imbach JL. Eur. J. Med. Chem. 1992, 27: 809

Google Scholar
21 Sheldrick G. M. SHELXTL PLUS. PC version. A System of Computer Programs for the Determination of Crystal Structure from X-ray Diffraction Data. Rev. 5.1. University of Göttingen; Germany: 1998.

Google Scholar

17

To be precise, the material recovered from the reaction exhibited the same ^¹H and ^¹³C NMR spectra as that of compound 6b, but differed in melting point and elemental analysis, having significant lack of Cl. Probably, it was a mixture of the salts 6b with different counterions, namely chloride, hydroxide, and, maybe, borate. Treatment of this material with HCl afforded compound 6b identical with the authentic sample in all parameters.

20

Full crystallographic parameters have been deposited at the Cambridge Crystallographic Data Centre under reference number CCDC 702208. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44(1223)336-033; e-mail: deposit@ccdc.cam.ac.uk].